Optical film having antistatic layer, polarizing plate and image display device

ABSTRACT

An optical film includes a transparent support and at least one antistatic layer formed from a composition containing an electrically conductive polymer, a polyfunctional monomer having two or more polymerizable groups, at least one compound selected from a compound represented by the formula (1) as defined herein, a compound represented by the formula (2) as defined herein and a trivalent phosphorus compound, and a photopolymerization initiator.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims the benefit of Japanese Patent Application JP2009-203144, filed Sep. 2, 2009, the entire content of which is herebyincorporated by reference, the same as if set forth at length.

FIELD OF THE INVENTION

The present invention relates to an optical film having an antistaticlayer, a polarizing plate using the optical film, and an image displaydevice using the optical film or the polarizing plate on the outermostsurface of the display.

BACKGROUND OF THE INVENTION

In the fields of optics, precision machines, building materials, homeelectronics and so forth, lamination of a film having an antistaticability is supposed to be useful for the purpose of preventing dustattachment, electric circuit failure and the like. Above all, in thefield of home electronics, from the standpoint of preventing dusts oravoiding a failure during panel fabrication, an antistatic property isrequired of the protective film applied to an image display device suchas a cathode ray tube (CRT), plasma display panel (PDP),electroluminescent display (ELD) and liquid crystal display (LCD).

In addition to the antistatic property, various functions such as glareprevention, antireflection, hardcoat performance and antifoulingproperty are sometimes required of the protective film of theabove-described image display device, and it is important to satisfythese functions all at the same time.

As for the method to impart an antistatic performance to an optical filmused in an image display device, an antireflection film having a layerwhere electrically conductive inorganic metal oxide particles aredispersed in an organic binder has been conventionally known (see,JP-A-2005-196122 (the term “JP-A” as used herein means an “unexaminedpublished Japanese patent application”)). However, the refractive indexof an electrically conductive particle conventionally used in general isas high as approximately from 1.6 to 2.2 and therefore, when aninorganic metal oxide particle is used in an optical film, therefractive index of the layer containing such a particle is increased.The increase in the refractive index of the layer may allow foroccurrence of unintended interference fringe due to a difference in therefractive index from an adjacent layer or may cause a problem such asintensified tint of the reflected color.

On the other hand, an electrically conductive polymer is known as anelectrically conductive material replacing the inorganic oxide particle.For example, a polythiophene containing a polyanion has been developedas the electrically conductive polymer, and a technique of forming anelectrically conductive film using the polymer is disclosed (EuropeanPatent No. 440,957). This electrically conductive film is not high inthe refractive index as compared with an inorganic fineparticle-containing antistatic film, but because the film is formed ofan electrically conductive polymer alone, the strength of the coat isweak and its application as a protective film has a problem.

To cope with this problem, a coating film composed of an electricallyconductive polymer and a curable binder is disclosed (JP-A-2004-91618and JP-A-2006-176681). However, such a technique is disadvantageous inthat the durability such as light resistance, heat resistance and wetheat resistance, particularly light resistance, is poor and theelectrical conductivity is significantly impaired due to lightirradiation.

Meanwhile, for enhancing the wet heat resistance, it has been proposedto use an electrically conductive polymer in which a hydroxygroup-containing aromatic compound having two or more hydroxyl groupsbonded to the aromatic ring is mixed (JP-A-2006-131873).

SUMMARY OF THE INVENTION

In the technique of JP-A-2006-131873, however, it has been found thatwhen an electrically conductive polymer is used in combination with ageneral hardcoat material which is cured by radical polymerization, theabove-described hydroxyl group-containing aromatic compound sometimesfunctions as a radical trapping agent to inhibit the polymerization andallow for no proceeding of curing of the coating film.

In particular, a coating film having a low density of the electricallyconductive polymer as a result of mixing of a curable binder and anelectrically conductive polymer suffers from significant deteriorationof the light resistance and can hardly satisfy not only the electricalconductivity but also the hardness and transmittance of the coatingfilm. More specifically, it has been found that a small content of theelectrically conductive polymer gives rise to bad durability and whenthe content is increased, this incurs a problem of reduction in thehardness of the coating film or reduction in the transmittance due tocoloring. In this respect, improvements are required.

The present invention has been made under these circumstances, and anobject of the present invention is to provide an optical film having anantistatic layer assured of high coat strength, excellent in thehardcoat performance, transparency and antistatic property and at thesame time, excellent in the heat resistance, wet heat resistance andlight resistance.

As a result of intensive studies to solve the problems above, thepresent inventors have discovered that when a compound (C) of thepresent invention described blow is used in combination in the mixtureof an electrically conductive polymer and a curable monomer, thoseproblems can be solved and the above-described object can be attained.The present invention has been accomplished based on this discovery.

[1] An optical film comprising a transparent support and at least oneantistatic layer formed from a composition containing at least thefollowing (A) to (D):

(A) an electrically conductive polymer,

(B) a polyfunctional monomer having two or more polymerizable groups,

(C) at least one kind of a compound selected from the following compound(1), the following compound (2) and the following compound (3), and

(D) a photopolymerization initiator:

Compound (1):

a compound represented by the following formula (1):

[wherein Y represents an m-valent group selected from a hydrogen atom, acarbon atom, a heteroatom, a hydroxy group, a mercapto group, asubstituted or unsubstituted group derived from an amino group, asubstituted or unsubstituted group derived from an alkyl group, asubstituted or unsubstituted group derived from an acyl group, asubstituted or unsubstituted group derived from an aryl group, asubstituted or unsubstituted group derived from an alkoxy group, asubstituted or unsubstituted group derived from an aryloxy group and asubstituted or unsubstituted group derived from a heteroaryl group, Lrepresents a single bond, a substituted or unsubstituted divalenthydrocarbon group, a substituted or unsubstituted divalent heteroatom,or a substituted or unsubstituted imino group, and m represents aninteger of 1 or more];Compound (2):

a compound represented by the following formula (2):

[wherein R₁ represents a hydrogen atom, an alkyl group, an acyl group,an aryl group, an alkoxy group, an aryloxy group or a heteroaryl group,R₂ represents a hydrogen atom, an alkyl group, an aryl group, aheteroaryl group or a sulfonyl group, and the alkyl group, acyl group,aryl group, alkoxy group, aryloxy group, heteroaryl group and sulfonylgroup each may have a substituent]; andCompound (3):

a trivalent phosphorus compound.

[2] The optical film as described in [1] above, wherein the commonlogarithmic value (LogSR) of the surface resistivity SR (Ω/sq) of theoptical film is from 6 to 12.

[3] The optical film as described in [1] or [2] above, wherein theelectrically conductive polymer (A) contains at least any one ofpolythiophene, polyaniline, polypyrrole and derivatives thereof.

[4] The optical film as described in [1] or [2] above, wherein theelectrically conductive polymer (A) contains at least any one ofpolythiophene and derivatives thereof.

[5] The optical film as described in [1] or [2] above, wherein theelectrically conductive polymer (A) containspoly(3,4-ethylenedioxy)thiophene.

[6] The optical film as described in any one of [1] to [5] above,wherein a polystyrenesulfonic acid is contained as a dopant of theelectrically conductive polymer (A).

[7] The optical film as described in any one of [1] to [6] above,wherein the compound (1) is a phosphonic acid compound.

[8] The optical film as described in any one of [1] to [7] above,wherein in formula (1), m is an integer of 2 or more.

[9] The optical film as described in any one of [1] to [8] above,wherein the compound represented by formula (2) contains at least onecompound selected from the group consisting of a hydroxamic acidcompound and a hydroxyamine compound.

[10] The optical film as described in any one of [1] to [9] above,wherein the trivalent phosphorus compound of the compound (3) is acompound represented by the following formula (I), (II), (III) or (IV):

[wherein each of R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹ and R¹²independently represents a hydrogen atom, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted aryl group, or a substitutedor unsubstituted heteroaryl group].

[11] The optical film as described in any one of [1] to [10] above,wherein the polymerizable group of the (B) polyfunctional monomer havingtwo or more polymerizable groups is any one group selected from asubstituted or unsubstituted acryloyl group, a substituted orunsubstituted methacryloyl group, and —C(O)OCH═CH₂.

[12] The optical film as described in any one of [1] to [11] above,wherein the composition further contains (F) a fluorine-containing orsilicon-containing surfactant.

[13] The optical film as described in any one of [1] to [12] above,wherein the compound (1) and the compound (2) are contained as thecomponent (C).

[14] The optical film as described in any one of [1] to [13] above,wherein the compound (1) and the compound (3) are contained as thecomponent (C).

[15] The optical film as described in any one of [1] to [14] above,wherein the antistatic layer contains a translucent particle having anaverage particle diameter of 0.5 to 20 μm (on the volume basis).

[16] An antireflection film having a low refractive index layer on theantistatic layer of the optical film described in any one of [1] to [15]above, directly or through another layer.

[17] A polarizing plate using the optical film described in any one of[1] to [15] above or the antireflection film described in [16] above, asa polarizing plate protective film.

[18] An image display device having the optical film described in anyone of [1] to [15] above, the antireflection film described in [16]above, or the polarizing plate described in [17] above, on the outermostsurface of the display.

According to the present invention, an optical film and anantireflection film, each having an antistatic layer assured of highcoat strength, excellent in the hardcoat performance, transparency andantistatic property and at the same time, excellent in the heatresistance, wet heat resistance and light resistance, and a polarizingplate and an image display device, each using the film, can be provided.

DETAILED DESCRIPTION OF THE INVENTION

The present invention is described in detail below.

The optical film of the present invention has, on a transparent support,at least one antistatic layer formed of a composition containing atleast the following (A) to (D). More specifically, the optical film canbe formed by applying a coating composition containing the followingcomponents (A) to (D) on a transparent support and curing the coating:

(A) an electrically conductive polymer,

(B) a polyfunctional monomer having two or more polymerizable groups,

(C) at least one kind of a compound selected from the following compound(1), the following compound (2) and the following compound (3), and

(D) a photopolymerization initiator:

Compound (1):

a compound represented by the following formula (1):

[wherein Y represents an m-valent group selected from a hydrogen atom, acarbon atom, a heteroatom, a hydroxy group, a mercapto group, asubstituted or unsubstituted group derived from an amino group, asubstituted or unsubstituted group derived from an alkyl group, asubstituted or unsubstituted group derived from an acyl group, asubstituted or unsubstituted group derived from an aryl group, asubstituted or unsubstituted group derived from an alkoxy group, asubstituted or unsubstituted group derived from an aryloxy group and asubstituted or unsubstituted group derived from a heteroaryl group, Lrepresents a single bond, a substituted or unsubstituted divalenthydrocarbon group, a substituted or unsubstituted divalent heteroatom,or a substituted or unsubstituted imino group, and m represents aninteger of 1 or more];Compound (2):

a compound represented by the following formula (2):

[wherein R₁ represents a hydrogen atom, an alkyl group, an acyl group,an aryl group, an alkoxy group, an aryloxy group or a heteroaryl group,R₂ represents a hydrogen atom, an alkyl group, an aryl group, aheteroaryl group or a sulfonyl group, and the alkyl group, acyl group,aryl group, alkoxy group, aryloxy group, heteroaryl group and sulfonylgroup each may have a substituent]; andCompound (3):

a trivalent phosphorus compound.

Each component contained in the antistatic layer according to thepresent invention is described below.

[(A) Electrically Conductive Polymer]

The electrically conductive polymer which can be used for the opticalfilm of the present invention is firs described.

The electrically conductive polymer for use in the present inventionindicates a polymer showing electrical conductivity of 10⁻⁶ S·cm⁻¹ ormore, and any compound may be used as long as it is a polymer compoundfalling under this class. A polymer compound having an electricalconductivity of 10⁻¹ S·cm⁻¹ or more is preferred.

The electrically conductive polymer is preferably a non-conjugatedpolymer or conjugated polymer in which aromatic carbocyclic rings oraromatic heterocyclic rings are linked by a single bond or a divalent orhigher-valent linking group. Examples of the aromatic carbocyclic ringin the non-conjugated polymer or conjugated polymer include a benzenering, and the ring may further form a fused ring. Examples of thearomatic heterocyclic ring in the non-conjugated polymer or conjugatedpolymer include a pyridine ring, a pyrazine ring, a pyrimidine ring, apyridazine ring, a triazine ring, an oxazole ring, a thiazole ring, animidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring,a tetrazole ring, a furan ring, a thiophene ring, a pyrrole ring, anindole ring, a carbazole ring, a benzimidazole ring and animidazopyridine ring, and the ring may further form a fused ring.

The divalent or higher-valent linking group in the non-conjugatedpolymer or conjugated polymer includes a linking group formed, forexample, by a carbon atom, a silicon atom, a nitrogen atom, a boronatom, an oxygen atom, a sulfur atom, a metal or a metal ion. The linkinggroup is preferably a group formed by a carbon atom, a nitrogen atom, asilicon atom, a boron atom, an oxygen atom, a sulfur atom or acombination thereof. Examples of the group formed by a combinationinclude a substituted or unsubstituted methylene group, a substituted orunsubstituted carbonyl group, a substituted or unsubstituted iminogroup, a substituted or unsubstituted sulfonyl group, a substituted orunsubstituted sulfinyl group, a substituted or unsubstituted estergroup, a substituted or unsubstituted amide group, and a substituted orunsubstituted silyl group.

Specific examples of the electrically conductive polymer includesubstituted or unsubstituted electrically conductive polyaniline,polyparaphenylene, polyparaphenylene vinylene, polythiophene, polyfuran,polypyrrole, polyselenophene, polyisothianaphthene, polyphenylenesulfide, polyacetylene, polypyridyl vinylene, polyazine, and derivativesthereof. One of these polymers may be used alone, or two or more thereofcan be used in combination according to the purpose.

Also, as long as the desired electrical conductivity can be obtained,the polymer can be used as a mixture with any other polymer having noelectrical conductivity, or a copolymer of a monomer capable ofconfiguring an electrically conductive polymer and any other monomerhaving no electrical conductivity may be used.

The electrically conductive polymer is preferably a conjugated polymer.Examples of the conjugated polymer include polyacetylene,polydiacetylene, poly(paraphenylene), polyfluorene, polyazulene,poly(paraphenylene sulfide), polypyrrole, polythiophene,polyisothianaphthene, polyaniline, poly(paraphenylene vinylene),poly(2,5-thienylene vinylene), a double chain-type conjugated polymer(e.g., polyperinaphthalene), a metallophthalocyanine-based polymer,other conjugated polymers (e.g., poly(paraxylylene),poly[α-(5,5′-bithiophenediyl)benzylidene]), and derivatives thereof.

Among these, poly(paraphenylene), polypyrrole, polythiophene,polyaniline, poly(paraphenylene vinylene) and poly(2,5-thienylenevinylene) are preferred, polythiophene, polyaniline, polypyrrole andderivatives thereof are more preferred, and at least any one ofpolythiophene and derivatives thereof is still more preferred.

These conjugated polymers each may have a substituent, and thesubstituent of these conjugated polymers includes the substituentdescribed as R¹¹ in formula (X) later.

In particular, from the standpoint of obtaining an optical filmsatisfying both high transparency and antistatic property, it ispreferred that the electrically conductive polymer has a partialstructure represented by the following formula (X) (that is, the polymeris polythiophene or a derivative thereof).

In formula (X), R¹¹ represents a substituent; m11 represents an integerof 0 to 2, and when m11 represents 2, the plurality of R¹¹'s may be thesame or different and may combine with each other to form a ring; andn¹¹ represents an integer of 1 or more.

Examples of the substituent represented by R¹¹ include an alkyl group(preferably having a carbon number of 1 to 20, more preferably a carbonnumber of 1 to 12, still more preferably a carbon number of 1 to 8;e.g., methyl, ethyl, isopropyl, tert-butyl, n-octyl, n-decyl,n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl), an alkenyl group(preferably having a carbon number of 2 to 20, more preferably a carbonnumber of 2 to 12, still more preferably a carbon number of 2 to 8;e.g., vinyl, allyl, 2-butenyl, 3-pentenyl, 2-hexenyl, 3-hexenyl,4-hexenyl, 2-octenyl), an alkynyl group (preferably having a carbonnumber of 2 to 20, more preferably a carbon number of 2 to 12, stillmore preferably a carbon number of 2 to 8; e.g., propargyl, 3-pentynyl),an aryl group (preferably having a carbon number of 6 to 30, morepreferably a carbon number of 6 to 20, still more preferably a carbonnumber of 6 to 12; e.g., phenyl, p-methylphenyl, naphthyl), an aminogroup (preferably having a carbon number of 0 to 20, more preferably acarbon number of 0 to 10, still more preferably a carbon number of 0 to6; e.g., amino, methylamino, dimethylamino, diethylamino, dibenzylamino,diphenylamino),

an alkoxy group (preferably having a carbon number of 1 to 20, morepreferably a carbon number of 1 to 12, still more preferably a carbonnumber of 1 to 8; e.g., methoxy, ethoxy, butoxy, hexyloxy, octyloxy), anaryloxy group (preferably having a carbon number of 6 to 20, morepreferably a carbon number of 6 to 16, still more preferably a carbonnumber of 6 to 12; e.g., phenyloxy, 2-naphthyloxy), an acyl group(preferably having a carbon number of 1 to 20, more preferably a carbonnumber of 1 to 16, still more preferably a carbon number of 1 to 12;e.g., acetyl, benzoyl, formyl, pivaloyl), an alkoxycarbonyl group(preferably having a carbon number of 2 to 20, more preferably a carbonnumber of 2 to 16, still more preferably a carbon number of 2 to 12;e.g., methoxycarbonyl, ethoxycarbonyl), an aryloxycarbonyl group(preferably having a carbon number of 7 to 20, more preferably a carbonnumber of 7 to 16, still more preferably a carbon number of 7 to 10;e.g., phenyloxycarbonyl),

an acyloxy group (preferably having a carbon number of 2 to 20, morepreferably a carbon number of 2 to 16, still more preferably a carbonnumber of 2 to 10; e.g., acetoxy, benzoyloxy), an acylamino group(preferably having a carbon number of 2 to 20, more preferably a carbonnumber of 2 to 16, still more preferably a carbon number of 2 to 10;e.g., acetylamino, benzoylamino), an alkoxycarbonylamino group(preferably having a carbon number of 2 to 20, more preferably a carbonnumber of 2 to 16, still more preferably a carbon number of 2 to 12;e.g., methoxycarbonylamino), an aryloxycarbonylamino group (preferablyhaving a carbon number of 7 to 20, more preferably a carbon number of 7to 16, still more preferably a carbon number of 7 to 12; e.g.,phenyloxycarbonylamino), a sulfonylamino group (preferably having acarbon number of 1 to 20, more preferably a carbon number of 1 to 16,still more preferably a carbon number of 1 to 12; e.g.,methanesulfonylamino, benzenesulfonylamino), a sulfamoyl group(preferably having a carbon number of 0 to 20, more preferably a carbonnumber of 0 to 16, still more preferably a carbon number of 0 to 12;e.g., sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl),

a carbamoyl group (preferably having a carbon number of 1 to 20, morepreferably a carbon number of 1 to 16, still more preferably a carbonnumber of 1 to 12; e.g., carbamoyl, methylcarbamoyl, diethylcarbamoyl,phenylcarbamoyl), an alkylthio group (preferably having a carbon numberof 1 to 20, more preferably a carbon number of 1 to 16, still morepreferably a carbon number of 1 to 12; e.g., methylthio, ethylthio), anarylthio group (preferably having a carbon number of 6 to 20, morepreferably a carbon number of 6 to 16, still more preferably a carbonnumber of 6 to 12; e.g., phenylthio), a sulfonyl group (preferablyhaving a carbon number of 1 to 20, more preferably a carbon number of 1to 16, still more preferably a carbon number of 1 to 12; e.g., mesyl,tosyl), a sulfinyl group (preferably having a carbon number of 1 to 20,more preferably a carbon number of 1 to 16, still more preferably acarbon number of 1 to 12; e.g., methanesulfinyl, benzenesulfinyl), aureido group (preferably having a carbon number of 1 to 20, morepreferably a carbon number of 1 to 16, still more preferably a carbonnumber of 1 to 12; e.g., ureido, methylureido, phenylureido), aphosphoric acid amide group (preferably having a carbon number of 1 to20, more preferably a carbon number of 1 to 16, still more preferably acarbon number of 1 to 12; e.g., diethylphosphoric acid amide,phenylphosphoric acid amide),

a hydroxy group, a mercapto group, a halogen atom (e.g., fluorine,chlorine, bromine, iodine), a cyano group, a sulfo group, a carboxylgroup, a nitro group, a hydroxamic acid group, a sulfino group, ahydrazino group, an imino group, a heterocyclic group (preferably havinga carbon number of 1 to 20, more preferably a carbon number of 1 to 12;examples of the heteroatom include a nitrogen atom, an oxygen atom and asulfur atom; specifically, for example, pyrrolidine, piperidine,piperazine, morpholine, thiophene, furan, pyrrole, imidazole, pyrazole,pyridine, pyrazine, pyridazine, triazole, triazine, indole, indazole,purine, thiazoline, thiazole, thiadiazole, oxazoline, oxazole,oxadiazole, quinoline, isoquinoline, phthalazine, naphthylidine,quinoxaline, quinazoline, cinnoline, pteridine, acridine,phenanthroline, phenazine, tetrazole, benzimidazole, benzoxazole,benzothiazole, benzotriazole and tetrazaindene), and a silyl group(preferably having a carbon number of 3 to 40, more preferably a carbonnumber of 3 to 30, still more preferably a carbon number of 3 to 24;e.g., trimethylsilyl, triphenylsilyl).

The substituent represented by R¹¹ may be further substituted. Also,when the substituent has a plurality of substituents, these substituentsmay be the same or different and, if possible, may combine with eachother to form a ring. Examples of the ring formed include a cycloalkylring, a benzene ring, a thiophene ring, a dioxane ring and a dithianering. The substituent represented by R¹¹ is preferably an alkyl group,an alkenyl group, an alkynyl group, an alkoxy group or an alkylthiogroup, more preferably an alkyl group, an alkoxy group or an alkylthiogroup. In particular, it is preferred that m11 is 2 and two R¹¹'s arealkoxy groups or alkylthio groups and form a ring, more preferably adioxane ring or a dithiane ring.

In formula (X), when m11 is 1, R¹¹ is preferably an alkyl group, morepreferably an alkyl group having a carbon number of 2 to 8.

Also, when R¹¹ is a poly(3-alkylthiophene) that is an alkyl group, thelinkage mode between adjacent thiophene rings includes a stericallyregular mode in which all rings are linked by a 2-5′ linkage, and asterically irregular mode containing a 2-2′ linkage and a 5-5′ linkage.A sterically irregular mode is preferred.

In the present invention, from the standpoint of satisfying both hightransparency and high electrical conductivity, the electricallyconductive polymer is more preferably poly(3,4-ethylenedioxy)thiophene(PEDOT, Compound (6) in specific examples shown below).

The polythiophene represented by formula (X) and derivatives thereof canbe produced by a known method described, for example, in J. Mater.Chem., 15, 2077-2088 (2005) and Advanced Materials, 12(7), page 481(2000). Also, these are available as a commercial product such asDenatron P502 (produced by Nagase ChemteX Corporation); and3,4-ethylenedioxythiophene (BAYTRON (registered trademark) M V2)3,4-polyethylenedioxythiopene/polystyrenesulfonate (BAYTRON (registeredtrademark) P), BAYTRON (registered trademark) C, BAYTRON (registeredtrademark) F E, BAYTRON (registered trademark) M V2, BAYTRON (registeredtrademark) P, BAYTRON (registered trademark) P AG, BAYTRON (registeredtrademark) P HC V4, BAYTRON (registered trademark) P HS, BAYTRON(registered trademark) PH, BAYTRON (registered trademark) PH 500, andBAYTRON (registered trademark) PH 510 (all produced by H.C. StarckGmbH).

As to the polyaniline and derivatives thereof, for example, Polyaniline(produced by Aldrich Chemical Company, Inc.) and Polyaniline (emeraldinesalt) (produced by Aldrich Chemical Company, Inc.) are available.

Specific examples of the electrically conductive polymer are illustratedbelow, but the present invention is not limited thereto. Other examplesinclude the compounds described in International Publication No.WO98/01909.

The weight average molecular weight of the electrically conductivepolymer for use in the present invention is preferably from 1,000 to1,000,000, more preferably from 10,000 to 500,000, still more preferablyfrom 10,000 to 100,000. The weight average molecular weight as usedherein is a polystyrene-equivalent weight average molecular weightmeasured by gel permeation chromatography.

(Solubility in Organic Solvent)

In view of coatability and imparting affinity for the component (B), theelectrically conductive polymer is preferably soluble in an organicsolvent.

More specifically, the electrically conductive polymer for use in thepresent invention is preferably soluble in an amount of at least 1.0mass % in an organic solvent having a water content of 5 mass % and arelative permittivity of 2 to 30.

The term “soluble” as used herein indicates that the polymer isdissolved in a single molecular state or in a state of a plurality ofsingle molecules being associated or is dispersed as particles having aparticle diameter of 300 nm or less.

In general, the electrically conductive polymer has high hydrophilicityand is conventionally dissolved in a solvent mainly composed of water.In order to solubilize such an electrically conductive polymer in anorganic solvent, a method of adding a compound capable of increasing theaffinity for an organic solvent (for example, the later-describedsolubilization aid) to a composition containing the electricallyconductive polymer, or a method of adding a dispersant or the like tothe organic solvent may be employed. Also, in the case of using anelectrically conductive polymer and a polyanion dopant, as describedlater, a hydrophobing treatment of the polyanion dopant is preferablyperformed.

Furthermore, there may be used a method where an electrically conductivepolymer in a dedoped state (in a state of not using a dopant) isenhanced in the organic solvent solubility and a dopant is added afterthe formation of a coated film to develop the electrical conductivity.

In addition, the methods described in the following literatures are alsopreferably used as the method for enhancing the solubility in an organicsolvent.

For example, JP-A-2002-179911 describes a method where a polyanilinecomposition in a dedoped state is dissolved in an organic solvent, theresulting material is coated on a substrate and dried, and the coatingis subjected to an oxidation and doping treatment to develop theelectrical conductivity.

Also, International Publication No. 05/035626 describes a method forproducing an electrically conductive polyaniline, where at the time ofoxidatively polymerizing aniline or a derivative thereof in a mixedlayer composed of an aqueous layer and an organic layer in the presenceof at least one of a sulfonic acid and a water-insoluble organic polymercompound having a protonic acid group, a molecular weight modifier and,if desired, a phase-transfer catalyst are caused to be present togetherand thereby, the polymer is stably dispersed in an organic solvent.

For example, alcohols, aromatic hydrocarbons, ethers, ketones and estersare suitable as the organic solvent. Specific examples of thesecompounds are described below (the relative permittivity is shown in theparenthesis).

The alcohols include, for example, a monohydric alcohol and a dihydricalcohol. Of these, the monohydric alcohol is preferably a saturatedaliphatic alcohol having a carbon number of 2 to 8. Specific examples ofthe alcohols include ethyl alcohol (25.7), n-propyl alcohol (21.8),i-propyl alcohol (18.6), n-butyl alcohol (17.1), sec-butyl alcohol(15.5) and tert-butyl alcohol (11.4).

Specific examples of the aromatic hydrocarbons include benzene (2.3),toluene (2.2) and xylene (2.2); specific examples of the ethers includetetrahydrofuran (7.5), ethylene glycol monomethyl ether (16), ethyleneglycol monomethyl ether acetate (8), ethylene glycol monoethyl ether(14), ethylene glycol monoethyl ether acetate (8) and ethylene glycolmonobutyl ether (9); specific examples of the ketones include acetone(21.5), diethyl ketone (17.0), methyl ethyl ketone (15.5), diacetonealcohol (18.2), methyl isobutyl ketone (13.1) and cyclohexanone (18.3);and specific examples of the esters include methyl acetate (7.0), ethylacetate (6.0), propyl acetate (5.7) and butyl acetate (5.0).

From the standpoint that both the electrically conductive polymer andthe (B) polyfunctional monomer having two or more polymerizable groupscan be dissolved and dispersed, the relative permittivity of the organicsolvent is preferably 2.3 to 24, more preferably from 4.0 to 21, andmost preferably from 5.0 to 21. For example, i-propyl alcohol, acetone,propylene glycol monoethyl ether, cyclohexanone and methyl acetate arepreferred, and i-propyl alcohol, acetone and propylene glycol monoethylether are more preferred.

In the present invention, the relative permittivity indicates a valuemeasured at 20° C.

A mixture of two or more kinds of organic solvents having a relativepermittivity of 2 to 30 may also be used. An organic solvent having arelative permittivity exceeding 30, or water in an amount of 5 mass % orless may be used in combination, but it is preferred that in the mixedorganic solvent system containing the organic solvent described above,the mass average relative permittivity of a plurality of organicsolvents or water does not exceed 30. Within this range, a coatingcomposition where both the electrically conductive polymer and the (B)polyfunctional monomer having two or more polymerizable groups aredissolved or dispersed can be formed, and a laminate having a goodsurface profile of the coating film can be obtained.

The water content of the organic solvent is preferably from 0 to 5 mass%, more preferably from 0 to 1 mass %.

The electrically conductive polymer is preferably soluble in an organicsolvent at a concentration of at least 1.0 mass %, more preferably at aconcentration of at least from 1.0 to 10.0 mass %, still more preferablyat a concentration of at least from 3.0 to 30.0 mass %.

In the organic solvent, the electrically conductive polymer may bepresent as particles. In this case, the average particle size ispreferably 300 nm or less, more preferably 200 nm or less, still morepreferably 100 nm or less. With the particle size in this range,precipitation of particles in the organic solvent can be suppressed. Thelower limit of the particle size is not particularly limited.

A high-pressure disperser may also be used so as to remove coarseparticles or accelerate the dissolution. Examples of the high-pressuredisperser include Gaulin (manufactured by A.P.V Gaulin Inc.), Nanomizer(manufactured by Nanomizer Inc.), Microfluidizer (manufactured byMicrofluidex Inc.), Altimizer (produced by Sugino Machine) and DeBee(manufactured by Bee International Ltd.). The particle size can beobserved after scooping an organic solvent solution on a grid forelectron microscopic observation and volatilizing the solvent.

(Hydrophobing Treatment)

As described above, in the case of using a polyanion dopant togetherwith the electrically conductive polymer, the composition containing theelectrically conductive polymer and the polyanion dopant is preferablysubjected to a hydrophobing treatment. By applying a hydrophobingtreatment to the composition above, solubility of the electricallyconductive polymer in an organic solvent can be increased, and theaffinity for the (B) polyfunctional monomer having two or morepolymerizable groups can be enhanced. The hydrophobing treatment can beperformed by modifying the anion group of the polyanion dopant.

More specifically, a first method for the hydrophobing treatmentincludes a method of esterifying, etherifying, acetylating, tosylating,tritylating, alkylsilylating or alkylcarbonylating the anion group.Above all, esterification and etherification are preferred. Examples ofthe method of performing hydrophobization by esterification include amethod of chlorinating the anion group of the polyanion dopant with achlorinating agent and then esterifying it with an alcohol such asmethanol and ethanol. The hydrophobization can also be performed byesterifying the anion group with a sulfo group or a carboxy group byusing a compound having a hydroxyl group or a glycidyl group and furtherusing a compound having an unsaturated double bonding group.

In the present invention, conventionally known various methods can beused, and these methods are specifically described, for example, inJP-A-2005-314671 and JP-2006-28439.

A second method for the hydrophobing treatment includes a method ofhydrophobing the anion group of the polyanion dopant by bonding a basiccompound thereto. The basic compound is preferably an amine-basedcompound, and examples thereof include a primary amine, a secondaryamine, a tertiary amine and an aromatic amine. specific examples thereofinclude a primary to tertiary amine substituted with an alkyl grouphaving a carbon number of 1 to 20, an imidazole or pyridine substitutedwith an alkyl group having a carbon number of 1 to 20. for enhancing thesolubility in an organic solvent, the molecular weight of the amine ispreferably from 50 to 2,000, more preferably from 70 to 1,000, and mostpreferably from 80 to 500.

The amount of the amine compound that is a basic hydrophobing agent ispreferably from 0.1 to 10.0 molar equivalents, more preferably from 0.5to 2.0 molar equivalents, still more preferably from 0.85 to 1.25 molarequivalents, based on the anion group of the polyanion dopant notcontributing to doping of the electrically conductive polymer. Withinthis range, the solubility in an organic solvent, the electricalconductivity and the strength of the coating film can be satisfied.

As for other details of the hydrophobing treatment, the mattersdescribed, for example, in JP-A-2008-115215 and JP-A-2008-115216 can beapplied.

(Solubilization Aid)

The electrically conductive polymer can be used together with a compoundcontaining a hydrophilic moiety, a hydrophobic moiety and, preferably,an ionizing radiation-curable functional group-containing moiety in themolecule (hereinafter referred to as a “solubilization aid”).

Use of a solubilization aid assists in solubilizing the electricallyconductive polymer in an organic solvent having a low water content andfurthermore, makes it possible to improve the coated surface state of alayer formed of the composition of the present invention or increase thestrength of the cured film.

The solubilization aid is preferably a copolymer having a hydrophilicmoiety, a hydrophobic moiety and an ionizing radiation-curablefunctional group-containing moiety, more preferably a block or graftcopolymer in which these moieties divided into segments. Such acopolymer can be polymerized by living anionic polymerization or livingradical polymerization or by using macromonomers having the moietiesabove.

The solubilization aid is described, for example, in JP-A-2006-176681,paragraphs [0022] to [0038].

(Preparation Method of Solution Containing Electrically ConductivePolymer)

The electrically conductive polymer can be prepared in the form of asolution by using the organic solvent described above.

The method for preparing an electrically conductive polymer solutionincludes several methods, but the following three methods are preferred.

The first method is a method of polymerizing an electrically conductivepolymer in water in the co-presence of a polyanion dopant, treating thepolymer, if desired, by adding the above-described solubilization aid orbasic hydrophobing agent, and then replacing the water with an organicsolvent. The second method is a method of polymerizing an electricallyconductive polymer in water in the co-presence of a polyanion dopant,treating the polymer, if desired, with the above-describedsolubilization aid or basic hydrophobing agent, evaporating the water todryness, and adding an organic solvent to solubilize the polymer. Thethird method is a method of separately preparing a π-conjugatedelectrically conductive polymer and a polyanion dopant, mixing anddispersing these two members in a solvent to prepare an electricallyconductive polymer composition in a doped state, and when the solventcontains water, replacing the water with an organic solvent.

In the methods above, the amount of the solubilization aid used ispreferably from 1 to 100 mass %, more preferably from 2 to 70 mass %,and most preferably from 5 to 50 mass %, based on the total amount ofthe electrically conductive polymer and the polyanion dopant. In thefirst method, the method for replacing water with an organic solvent ispreferably a method of preparing a uniform solution by adding and usinga solvent having high water miscibility, such as ethanol, isopropylalcohol and acetone, and then removing the water by ultrafiltration.Also, a method of reducing the water content to a certain extent byusing a solvent having high water miscibility, mixing a more hydrophobicsolvent, and removing highly volatile components under reduced pressureto prepare a solvent composition may be used. Furthermore, whensufficient hydrophobization is performed using a basic hydrophobingagent, it is also possible to separate the composition into a two-phasesystem by adding an organic solvent having low water miscibility andextract the organic electrically conductive polymer into the organicsolvent phase from the aqueous phase.

[(B) Polyfunctional Monomer Having Two or More Polymerizable UnsaturatedGroups]

In the present invention, the composition contains (B) a polyfunctionalmonomer having two or more polymerizable unsaturated groups. The (B)polyfunctional monomer having two or more polymerizable unsaturatedgroups can function as a curing agent. Thanks to a combination use of(A) an electrically conductive polymer and (B) a polyfunctional monomerhaving two or more polymerizable unsaturated groups, both the electricalconductivity and the strength or scratch resistance of the coating filmcan be satisfied. The number of polymerizable unsaturated groups ispreferably 3 or more.

The polyfunctional monomer having two or more polymerizable unsaturatedgroups, which is used in the present invention, is described below. Themonomer includes compounds having a polymerizable functional group suchas (meth)acryloyl group, vinyl group, styryl group, allyl group and—C(O)OCH═CH₂. Above all, any group selected from a substituted orunsubstituted acryloyl group, a substituted or unsubstitutedmethacryloyl group, and —C(O)OCH═CH₂ is preferred. A compound containingthree or more (meth)acryloyl groups within one molecule can be morepreferably used.

Specific examples of the compound having a polymerizable unsaturatedbond include (meth)acrylic acid diesters of alkylene glycol,(meth)acrylic acid diesters of polyoxyalkylene glycol, (meth)acrylicacid diesters of polyhydric alcohol, (meth)acrylic acid diesters ofethylene oxide or propylene oxide adduct, epoxy(meth)acrylates,urethane(meth)acrylates, and polyester(meth)acrylates.

Among these, esters of polyhydric alcohol and (meth)acrylic acid arepreferred. Examples thereof include pentaerythritol tetra(meth)acrylate,pentaerythritol tri(meth)acrylate, trimethylolpropane tri(meth)acrylate,EO-modified trimethylolpropane tri(meth)acrylate, PO-modifiedtrimethylolpropane tri(meth)acrylate, EO-modified phosphoric acidtri(meth)acrylate, trimethylolethane tri(meth)acrylate,ditrimethylolpropane tetra(meth)acrylate, dipentaerythritoltetra(meth)acrylate, dipentaerythritol penta(meth)acrylate,dipentaerythritol hexa(meth)acrylate, pentaerythritolhexa(meth)acrylate, 1,2,3-cyclohexane tetramethacrylate, polyurethanepolyacrylate, polyester polyacrylate, and caprolactone-modifiedtris(acryloxyethyl)isocyanurate.

As for the polyfunctional acrylate-based compounds having a(meth)acryloyl group, commercially available products may also be used,and examples thereof include KAYARAD DPHA and KAYARAD PET-30, producedby Nippon Kayaku Co., Ltd.

The non-fluorine-containing polyfunctional monomer is described inJP-A-2009-98658, paragraphs [0114] to [0122], and the same applies tothe present invention.

[(C) Compound (1), Compound (2) and Compound (3)]

The composition of an antistatic layer of the present invention containsat least any one of the compound (1), the compound (2) and the compound(3). By virtue of adding at least any one of the compound (1), thecompound (2) and the compound (3) to the composition for an antistaticlayer, an antistatic optical film excellent in the heat resistance, wetheat resistance and light resistance can be obtained.

<Compound (1)>

The compound (1) is a compound represented by the following formula (1).The reason why an optical film excellent in the light resistance and wetheat durability is obtained by containing a compound represented by thefollowing formula (1) in the antistatic layer is not clearly known, butthe compound (1) is considered to suppress dedoping of the electricallyconductive polymer and in turn, prevent the decomposition reactionassociated therewith.

In formula (1), Y represents an m-valent group selected from a hydrogenatom, a carbon atom, a heteroatom, a hydroxy group, a mercapto group, anamino group-derived group, an alkyl group-derived group, an acylgroup-derived group, an aryl group-derived group, an alkoxygroup-derived group, an aryloxy group-derived group and a heteroarylgroup-derived group, L represents a single bond, a divalent hydrocarbongroup, a divalent heteroatom or an imino group, and m represents aninteger of 1 or more.

In formula (1), Y each may have a substituent. The substituent includesthe following substituent group V:

(Substituent Group V)

a halogen atom (e.g., chlorine, bromine, iodine, fluorine); a mercaptogroup; a cyano group; a carboxyl group; a phosphoric acid group; a sulfogroup; a hydroxy group; a carbamoyl group having a carbon number of 1 to10, preferably a carbon number of 2 to 8, more preferably a carbonnumber of 2 to 5 (e.g., methylcarbamoyl, ethylcarbamoyl,morpholinocarbamoyl); a sulfamoyl group having a carbon number of 0 to10, preferably a carbon number of 2 to 8, more preferably a carbonnumber of 2 to 5 (e.g., methylsulfamoyl, ethylsulfamoyl,piperidinosulfamoyl); a nitro group; an alkoxy group having a carbonnumber of 1 to 20, preferably a carbon number of 1 to 10, morepreferably a carbon number of 1 to 8 (e.g., methoxy, ethoxy,2-methoxyethoxy 2-phenylethoxy); an aryloxy groups having a carbonnumber of 6 to 20, preferably a carbon number of 6 to 12, morepreferably a carbon number of 6 to 10 (e.g., phenoxy, p-methylphenoxy,p-chlorophenoxy, naphthoxy); an acyl groups having a carbon number of 1to 20, preferably a carbon number of 2 to 12, more preferably a carbonnumber of 2 to 8 (e.g., acetyl, benzoyl, trichloroacetyl); an acyloxygroups having a carbon number of 1 to 20, preferably a carbon number of2 to 12, more preferably a carbon number of 2 to 8 (e.g., acetyloxy,benzoyloxy); an acylamino group having a carbon number of 1 to 20,preferably a carbon number of 2 to 12, more preferably a carbon numberof 2 to 8 (e.g., acetylamino);

a sulfonyl group having a carbon number of 1 to 20, preferably a carbonnumber of 1 to 10, more preferably a carbon number of 1 to 8 (e.g.,methanesulfonyl, ethanesulfonyl, benzenesulfonyl); a sulfinyl grouphaving a carbon number of 1 to 20, preferably a carbon number of 1 to10, more preferably a carbon number of 1 to 8 (e.g., methanesulfinyl,ethanesulfinyl, benzenesulfinyl); a sulfonylamino group having a carbonnumber of 1 to 20, preferably a carbon number of 1 to 10, morepreferably a carbon number of 1 to 8 (e.g., methanesulfonylamino,ethanesulfonylamino, benzenesulfonylamino); a substituted orunsubstituted amino group having a carbon number of 0 to 20, preferablya carbon number of 0 to 12, more preferably a carbon number of 0 to 8(e.g., unsubstituted amino, methylamino, dimethylamino, benzylamino,anilino, diphenylamino); an ammonium group having a carbon number of 0to 15, preferably a carbon number of 3 to 10, more preferably a carbonnumber of 3 to 6 (e.g., trimethylammonium, triethylammonium); ahydrazino group having a carbon number of 0 to 15, preferably a carbonnumber of 1 to 10, more preferably a carbon number of 1 to 6 (e.g.,trimethylhydrazino); a ureido group having a carbon number of 1 to 15,preferably a carbon number of 1 to 10, more preferably a carbon numberof 1 to 6 (e.g., ureido, N,N-dimethylureido); an imido group having acarbon number of 1 to 15, preferably a carbon number of 1 to 10, morepreferably a carbon number of 1 to 6 (e.g., succinimide);

an alkylthio group having a carbon number of 1 to 20, preferably acarbon number of 1 to 12, more preferably a carbon number of 1 to 8(e.g., methylthio, ethylthio, propylthio); an arylthio group having acarbon number of 6 to 80, preferably a carbon number of 6 to 40, morepreferably a carbon number of 6 to 30 (e.g., phenylthio,p-methylphenylthio, p-chlorophenylthio, 2-pyridylthio, 1-naphthylthio,2-naphthylthio, 4-propylcyclohexyl-4′-biphenylthio,4-butylcyclohexyl-4′-biphenylthio, 4-pentylcyclohexyl-4′-biphenylthio,4-propylphenyl-2-ethynyl-4′-biphenylthio); a heteroarylthio group havinga carbon number of 1 to 80, preferably a carbon number of 1 to 40, morepreferably a carbon number of 1 to 30 (e.g., 2-pyridylthio,3-pyridylthio, 4-pyridylthio, 2-quinolylthio, 2-furylthio,2-pyrrolylthio); an alkoxycarbonyl group having a carbon number of 2 to20, preferably a carbon number of 2 to 12, more preferably a carbonnumber of 2 to 8 (e.g., methoxycarbonyl, ethoxycarbonyl,2-benzyloxycarbonyl); an aryloxycarbonyl group having a carbon number of6 to 20, preferably a carbon number of 6 to 12, more preferably a carbonnumber of 6 to 10 (e.g., phenoxycarbonyl);

an unsubstituted alkyl group having a carbon number of 1 to 18,preferably a carbon number of 1 to 10, more preferably a carbon numberof 1 to 5 (e.g., methyl, ethyl, propyl, butyl); a substituted alkylgroup having a carbon number of 1 to 18, preferably a carbon number of 1to 10, more preferably a carbon number of 1 to 5 {e.g., hydroxymethyl,trifluoromethyl, benzyl, carboxyethyl, ethoxycarbonylmethyl,acetylaminomethyl; here, the substituted alkyl group also includes anunsaturated hydrocarbon group having a carbon number of 2 to 18,preferably a carbon number of 3 to 10, more preferably a carbon numberof 3 to 5 (e.g., vinyl, ethynyl, 1-cyclohexenyl, benzylidine,benzylidene)}; a substituted or unsubstituted aryl group having a carbonnumber of 6 to 20, preferably a carbon number of 6 to 15, morepreferably a carbon number of 6 to 10 (e.g., phenyl, naphthyl,p-carboxyphenyl, p-nitrophenyl, 3,5-dichlorophenyl, p-cyanophenyl,m-fluorophenyl, p-tolyl, 4-propylcyclohexyl-4′-biphenyl,4-butylcyclohexyl-4′-biphenyl, 4-pentylcyclohexyl-4′-biphenyl,4-propylphenyl-2-ethynyl-4′-biphenyl); and a substituted orunsubstituted heterocyclic group having a carbon number of 1 to 20,preferably a carbon number of 2 to 10, more preferably a carbon numberof 4 to 6 (e.g., pyridyl, 5-methylpyridyl, thienyl, furyl, morpholino,tetrahydrofurfuryl).

Substituents of the substituent group V may form a structure in which abenzene ring or a naphthalene ring is fused.

Also, these substituents may be further substituted. The furthersubstituent includes any substituent selected from the substituent groupV.

In formula (1), m represents an integer of 1 or more. As describedlater, when Y is a polyvalent group, m is determined according to thevalence of the polyvalent group.

More specifically, in formula (1), when Y is a carbon atom, m is 4. Inthe case where Y is a heteroatom, m is 3 when a nitrogen atom, and m is2 when an oxygen atom or a sulfur atom. When Y is a hydrogen atom, ahydroxy group or a mercapto group, m is 1.

The heteroatom represented by Y in formula (1) is preferably a nitrogenatom, an oxygen atom, a sulfur atom or a selenium atom, more preferablya nitrogen atom, an oxygen atom or a sulfur atom.

The alkyl group-derived group represented by Y in formula (1) includes amonovalent (m=1) group, that is, an alkyl group, and a divalent (m=2)group, that is, an alkylene group, and further includes a group havingthree or more bonds. The same applies to the alkyl group present in thegroup derived from an alkoxy group.

The alkyl group-derived group represented by Y may be linear, branchedor cyclic. The alkyl group-derived group represented by Y preferably hasa carbon number of 1 to 60, more preferably a carbon number of 1 to 50,still more preferably a carbon number of 1 to 40.

Furthermore, in formula (1), the alkyl group-derived group representedby Y may be unsubstituted or may have a substituent. Examples of thesubstituent include the substituent group V. Among the substituent groupV, a halogen atom (fluorine, chlorine, bromine, iodine), a hydroxygroup, a mercapto group, an aryl group, a heteroaryl group, an acylgroup, an alkoxy group, an amino group, a cyano group, a carboxyl group,a sulfo group, a carbamoyl group, a sulfamoyl group, a nitro group, anaryloxy group, an acyloxy group and an acylamino group are preferred,and a halogen atom (fluorine), a hydroxy group, a mercapto group, anacyl group, an alkoxy group, an aryl group, a heteroaryl group, a sulfogroup and an aryloxy group are more preferred.

Specific examples of the alkyl group-derived group represented by Yinclude: when m=1, methyl, ethyl, tert-butyl, tert-octyl, 2-ethylhexyl,cyclohexyl, n-hexadecyl, 3-dodecyloxypropyl, perfluorobutyl and3-(2′,4′-di-tert-pentylphenoxy)propyl; when m=2, methylene, ethylene,methylhydroxymethylene and isobutylene; and when m=3, cyclohexanetriyland cyclohexanetetrayl.

In formula (1), the acyl group-derived group represented by Y includes amonovalent (m=1) group such as formyl group and acetyl group, and adivalent (m=2) group, that is, a carbonyl group. The acyl group-derivedgroup represented by Y in formula (1) preferably has a carbon number of1 to 60, more preferably a carbon number of 1 to 50, still morepreferably a carbon number of 1 to 40.

The acyl group-derived group represented by Y may be unsubstituted ormay have a substituent. Examples of the substituent include thesubstituent group V. Among the substituent group V, a halogen atom(fluorine, chlorine, bromine, iodine), an alkyl group, a hydroxy group,a mercapto group, an aryl group, a heteroaryl group, an acyl group, analkoxy group, an amino group, a cyano group, a carboxyl group, a sulfogroup, a carbamoyl group, a sulfamoyl group, a nitro group, an aryloxygroup, an acyloxy group and an acylamino group are preferred, and ahalogen atom, an alkyl group, a hydroxy group, a mercapto group, an arylgroup and a heteroaryl group are more preferred.

Specific examples of the acyl group-derived group represented by Yinclude: when m=1, acetyl, benzoyl, trichloroacetyl, phenylcarbonyl andethylcarbonyl; and when the group is polyvalent, carbonyl.

In formula (1), the aryl group-derived group represented by Y includes amonovalent (m=1) group, that is, an aryl group (e.g., phenyl, naphthyl),a divalent (m=2) group, that is, an arylene group (e.g., phenylene,naphthylene), and a polyvalent group such as triyl group and tetraylgroup. For example, the group derived from an unsubstituted phenyl groupcan take a monovalent to hexavalent form. The same applies to the arylgroup present in the aryloxy group-derived group.

The aryl group-derived group represented by Y preferably has a carbonnumber of 6 to 60, more preferably a carbon number of 6 to 50, stillmore preferably a carbon number of 6 to 40.

Furthermore, the aryl group-derived group represented by Y may beunsubstituted or may have a substituent, and examples of the substituentinclude the substituent group V. Among the substituent group V, an alkylgroup, an alkoxy group, a hydroxy group, a halogen atom (fluorine,chlorine, bromine, iodine), a mercapto group, an aryl group, aheteroaryl group, an acyl group, an amino group, a cyano group, acarboxyl group, a sulfo group, a carbamoyl group, a sulfamoyl group, anitro group, an aryloxy group, an acyloxy group and an acylamino groupare preferred. Also, the aryl group-derived group represented by Y maybe a polymer such as polystyrene. The number of repeating units in thepolymer is not particularly limited but, in view of solubility andantistatic property, the number of repeating units is preferably1,000,000 or less, more preferably 100,000 or less. The substituent ofthe aryl group-derived group represented by Y is more preferably analkyl group, an alkoxy group, a hydroxy group, a mercapto group, an acylgroup, an amino group, a carboxyl group, a sulfo group or a nitro group.

Specific examples of the aryl group-derived group represented by Yinclude: when m=1, phenyl, 1-naphthyl, 4-tolyl, 4-methoxyphenyl,4-hexadecyloxyphenyl, 3-pentadecylphenyl, 2,4-di-tert-pentylphenyl,8-quinolyl and 5 -(1-dodecyloxycarbonylethoxycarbonyl)-2-chlorophenyl;and when the group is polyvalent, o-phenylene, m-phenylene, p-phenylene,1,4-naphthylene, 9,10-anthrylene and 2-pentadecyl-1,4-phenylene.

The heteroaryl group-derived group represented by Y in formula (1)includes a monovalent (m=1) group, that is, a heteroaryl group, adivalent (m=2) group, that is, a heteroarylene group, and a polyvalentgroup such as triyl group and tetrayl group.

In formula (1), the heteroaryl group in the heteroaryl group-derivedgroup represented by Y is preferably a 5- to 8-membered heteroaryl groupcontaining at least one of a nitrogen atom, a sulfur atom, an oxygenatom and a selenium atom, as a heteroatom. Also, substituents of theheteroaryl group may combine with each other to form a ring, forexample, may form a fused ring together with an aromatic ring or thelike.

Furthermore, the heteroaryl group-derived group represented by Y may beunsubstituted or may have a substituent. Examples of the substituentinclude the substituent group V. Among the substituent group V, an alkylgroup, an alkoxy group, a hydroxy group, a halogen atom (fluorine,chlorine, bromine, iodine), a mercapto group, an aryl group, aheteroaryl group, an acyl group, an amino group, a cyano group, acarboxyl group, a sulfo group, a carbamoyl group, a sulfamoyl group, anitro group, an aryloxy group, an arylthio group, an acyloxy group andan acylamino group are preferred, and an alkyl group, an alkoxy group, ahydroxy group, a mercapto group, an acyl group, an amino group, acarboxyl group, a sulfo group and a nitro group are more preferred.

Specific examples of the heteroaryl group-derived group represented by Yinclude: when m=1, pyridyl, furyl, pyrrole, thiazolyl, oxazolyl,imidazolyl, triazolyl, tetrazolyl, benzotriazolyl and quinolyl; and whenthe group is polyvalent, pyridinediyl, imidazolylene, pyrrolylene andisothiazolylene.

Also, the heteroaryl group-derived group represented by Y may form asalt structure by allowing the heteroatom to become an ion. Examplesthereof include ammonium ion. In the case where the heteroatom is cationsuch as ammonium ion, the counter ion includes bromo ion, chloro ion,tetrafluoroborate ion, hexafluorophosphate ion, perchlorate ion andnitrate ion. In the case where the heteroatom is anion, the counter ionincludes ammonium ion, sodium ion, potassium ion and calcium ion.

The amino group-derived group represented by Y in formula (1) is anamino group (NH₂—) when m=1, and an imino group (—NH—) when m=2, but asubstituted amino group can be a polyvalent group depending on thesubstituent. For example, in the case of an alkylamino group, asdescribed above, the alkyl group contained as a substituent can be amonovalent group or a polyvalent group.

In formula (1), the amino group-derived group represented by Ypreferably has a carbon number of 1 to 100, more preferably a carbonnumber of 1 to 30, still more preferably a carbon number of 1 to 10.

The amino group-derived group represented by Y may be unsubstituted ormay have a substituent. Examples of the substituent include thesubstituent group V. Among the substituent group V, a hydroxy group, asulfo group, an alkyl group, an aryl group, a heteroaryl group, analkoxy group, a halogen atom (fluorine, chlorine, bromine, iodine), amercapto group and a carboxyl group are preferred, and a hydroxy group,a sulfo group and an alkyl group are more preferred.

Also, the amino group-derived group represented by Y may be ammoniumion. The counter ion includes bromo ion, chloro ion, tetrafluoroborateion, hexafluorophosphate ion, perchlorate ion and nitrate ion.

In formula (1), the alkoxy group-derived group represented by Y includesa monovalent (m=1) group, that is, an alkoxy group (e.g., methoxy,ethoxy), and a group where the alkyl moiety of the alkoxy group is apolyvalent group. For example, in the case where the alkyl moiety is analkylene group, the alkoxy group-derived group is a divalent (m=2)group, and in the case of a triylalkane, tetraylalkane or the like, thegroup is a trivalent or higher valent (m≧3) group. Furthermore, when thealkoxy group has a substituent and is substituted with a divalent (m=2)substituent or a polyvalent substituent such as triyl group and tetraylgroup, the alkoxy group-derived group becomes a polyvalent group. Forexample, an alkoxy group substituted with a trivalent substituentbecomes a divalent (m=2) group.

The alkoxy group-derived group represented by Y in formula (1) is analkoxy group preferably having a carbon number of 1 to 60, morepreferably a carbon number of 1 to 50, still more preferably a carbonnumber of 1 to 40.

Furthermore, the alkoxy group-derived group represented by Y may beunsubstituted or may have a substituent, and examples of the substituentinclude the substituent group V. Among the substituent group V, an alkylgroup, an alkoxy group, a hydroxy group, a halogen atom (fluorine,chlorine, bromine, iodine), a mercapto group, an aryl group, aheteroaryl group, an acyl group, an amino group, a cyano group, acarboxyl group, a sulfo group, a carbamoyl group, a sulfamoyl group, anitro group, an aryloxy group, an arylthio group, an acyloxy group andan acylamino group are preferred, and an alkyl group, an alkoxy group, ahydroxy group, a mercapto group, an aryl group and a heteroaryl groupare more preferred.

Specific examples of the alkoxy group-derived group represented by Yinclude: when m=1, methoxy, ethoxy, butoxy, methoxyethoxy andn-octyloxy; and when the group is polyvalent, ethylenedioxy andpropylenedioxy.

In formula (1), the aryloxy group-derived group represented by Yincludes a monovalent (m=1) group, that is, an aryloxy group (e.g.,phenoxy), and a group where the aryl moiety of the aryloxy group ispolyvalent. For example, in the case where the aryl moiety is trivalentand is an arylene group, the aryloxy group-derived group becomes adivalent (m=2) group.

Furthermore, in the case where the aryloxy group has a substituent andis substituted with a polyvalent substituent such as triyl group andtetrayl group, the aryloxy group-derived group becomes a polyvalentgroup. For example, an aryloxy group substituted with a triyl alkylgroup-derived group becomes a divalent (m=2) group.

In formula (1), the aryloxy group-derived group represented by Y is anaryloxy group preferably having a carbon number of 6 to 60, morepreferably a carbon number of 6 to 50, still more preferably a carbonnumber of 6 to 40.

Furthermore, the aryloxy group-derived group represented by Y may beunsubstituted or may have a substituent, and examples of the substituentinclude the substituent group V. Among the substituent group V, an alkylgroup, an alkoxy group, a hydroxy group, a halogen atom (fluorine,chlorine, bromine, iodine), a mercapto group, an aryl group, aheteroaryl group, an acyl group, an amino group, a cyano group, acarboxyl group, a sulfo group, a carbamoyl group, a sulfamoyl group, anitro group, an aryloxy group, an arylthio group, an acyloxy group andan acylamino group are preferred, and an alkyl group, an alkoxy group, ahydroxy group, a mercapto group, an amino group, a carboxyl group and asulfo group are more preferred.

Specific examples of the aryloxy group-derived group represented by Yinclude: when m=1, phenoxy, 4-tert-octylphenoxy, naphthyloxy andpyrenyloxy; and when the group is polyvalent, p-phenylenedioxy,naphthylenedioxy and 2-n-hexyl-1,4-phenylenedioxy.

In formula (1), L represents a single bond, a divalent hydrocarbongroup, a divalent heteroatom or an imino group.

In formula (1), the divalent hydrocarbon group represented by Lpreferably has a carbon number of 0 to 30, more preferably a carbonnumber of 0 to 20, still more preferably a carbon number of 0 to 10. Thedivalent hydrocarbon group represented by L may have a ring structureand/or an unsaturated bond in the hydrocarbon structure and ispreferably a saturated hydrocarbon group.

Also, the divalent hydrocarbon group represented by L may be linear orbranched and is preferably a linear hydrocarbon group.

Furthermore, the divalent hydrocarbon group represented by L may beunsubstituted or may have a substituent and is preferably anunsubstituted hydrocarbon group. Examples of the substituent include thesubstituent group V. Among the substituent group V, a halogen atom(fluorine, chlorine, bromine, iodine), a hydroxy group, a mercaptogroup, an aryl group, a heteroaryl group, an acyl group, an alkoxygroup, an amino group, a cyano group, a carboxyl group, a sulfo group, acarbamoyl group, a sulfamoyl group, a nitro group, an aryloxy group, anacyloxy group and an acylamino group are preferred, and a halogen atom(fluorine), a hydroxy group, a mercapto group, an acyl group, an alkoxygroup, an aryl group, a heteroaryl group, a sulfo group and an aryloxygroup are more preferred.

The divalent hydrocarbon group represented by L is more preferably anunsubstituted linear hydrocarbon group, still more preferably anunsubstituted linear hydrocarbon group having a carbon number of 0 to10.

In formula (1), the divalent heteroatom represented by L is an oxygenatom, a sulfur atom, a selenium atom or a nitrogen atom, preferably anoxygen atom, a sulfur atom or a selenium atom.

L in formula (1) is preferably a single bond, a divalent hydrocarbongroup, an oxygen atom, an imino group (—NH—, —NR— (R represents an alkylgroup, an aryl group or a heteroaryl group)), a sulfur atom or aselenium atom, more preferably a single bond or an unsubstituted lineardivalent hydrocarbon group.

In formula (1), m is preferably 2 or more in terms of high effect ofimproving the durability (light resistance, heat resistance, wet heatresistance), particularly the light resistance.

Specific examples of the compound represented by formula (1) for use inthe present invention are illustrated below, but the compoundrepresented by formula (1) of the present invention is not limited tothese specific examples.

The compound represented by formula (1) can be synthesized by a knownmethod. More specifically, a method of reacting an alcohol or halidecorresponding to “Y-L_(m)” in formula (1) with diphosphorus pentoxide orphosphoric acid to synthesize the compound is suitably used. Also, someof the compounds represented by formula (1) are available as acommercial product, and examples thereof include1-hydroxyethane-1,1-diphosphonic acid (produced by Tokyo ChemicalIndustry Co., Ltd.), nitrilotris(methylenephosphonic acid) (produced byTokyo Chemical Industry Co., Ltd.), and phytic acid (produced by TokyoChemical Industry Co., Ltd.).

In view of improving the light resistance and heat resistance, thecompound represented by formula (1) is preferably a phosphonic acidcompound. The “phosphonic acid compound” as used herein indicates acompound where in formula (1), the atom directly bonded to thephosphorus atom (P) on the Y side is not an oxygen atom.

The ratio between the compound represented by formula (1) and theelectrically conductive polymer in the antistatic layer may be anyratio, but from the standpoint of satisfying both high antistaticproperty and high durability, the ratio (compound represented by formula(1): electrically conductive polymer) is, in terms of mass ratio,preferably from 0.01:1.0 to 10:1, more preferably from 0.05:1.0 to5.0:1, still more preferably from 0.05:1.0 to 1.0:1.0.

<Compound (2)>

The compound (2) is a compound represented by the following formula (2).The compound represented by the following formula (2) (compound (2)scarcely causes aggregation even when the compound is present togetherwith the above-described electrically conductive polymer. Accordingly,an antistatic layer formed using a composition containing a compoundrepresented by the following formula (2) and the electrically conductivepolymer exhibits high transparency and good antistatic property and isexcellent in the light resistance, heat resistance and wet heatresistance. Formula (2):

In formula (2), R₁ represents a hydrogen atom, an alkyl group, an acylgroup, an aryl group, an alkoxy group, an aryloxy group or a heteroarylgroup. In formula (2), R₂ represents a hydrogen atom, an alkyl group, anaryl group, a heteroaryl group or a sulfonyl group. The alkyl group,acyl group, aryl group, alkoxy group, aryloxy group, heteroaryl groupand sulfonyl group may have a substituent.

R₁ and R₂ in formula (2) each may have a substituent. Examples of thesubstituent include the substituent group V.

The alkyl group represented by R₁ in formula (2) is preferably an alkylgroup having a carbon number of 1 to 60, more preferably a carbon numberof 1 to 50, still more preferably a carbon number of 1 to 40. Specificexamples thereof include methyl, tert-butyl, tert-octyl, 2-ethylhexyl,cyclohexyl, n-hexadecyl, 3-dodecyloxypropyl and3-(2′,4′-di-tert-pentylphenoxy)propyl.

The acyl group represented by R₁ in formula (2) is preferably an acylgroup having a carbon number of 1 to 60, more preferably a carbon numberof 1 to 50, still more preferably a carbon number of 1 to 40. Specificexamples thereof include acetyl, benzoyl, trichloroacetyl,phenylcarbonyl and ethylcarbonyl.

The aryl group represented by R₁ in formula (2) is preferably an arylgroup having a carbon number of 6 to 60, more preferably a carbon numberof 6 to 50, still more preferably a carbon number of 6 to 40. Specificexamples thereof include phenyl, 1-naphthyl, p-tolyl, o-tolyl,4-methoxyphenyl, 4-hexadecyloxyphenyl, 3-pentadecylphenyl,2,4-di-tert-pentylphenyl, 8-quinolyl and 5-(1-dodecyloxycarbonylethoxycarbonyl)-2-chlorophenyl.

The alkoxy group represented by R₁ in formula (2) is preferably analkoxy group having a carbon number of 1 to 60, more preferably a carbonnumber of 1 to 50, still more preferably a carbon number of 1 to 40.Specific examples thereof include methoxy, ethoxy, butoxy, methoxyethoxyand n-octyloxy.

The aryloxy group represented by R₁ in formula (2) is preferably anaryloxy group having a carbon number of 6 to 60, more preferably acarbon number of 6 to 50, still more preferably a carbon number of 6 to40. Specific examples thereof include phenoxy and 4-tert-octylphenoxy.

The heteroaryl group represented by R₁ in formula (2) is preferably a 5-to 8-membered heteroaryl group containing at least one heteroatomselected from N, S, O and Se. Specific examples thereof include4-pyridyl, 2-furyl, 2-pyrrole, 2-thiazolyl, 3-thiazolyl, 2-oxazolyl,2-imidazolyl, triazolyl, tetrazolyl, benzotriazolyl, 2-quinolyl and3-quinolyl.

The alkyl group represented by R₂ in formula (2) is preferably an alkylgroup having a carbon number of 1 to 60, more preferably a carbon numberof 1 to 50, still more preferably a carbon number of 1 to 40. Specificexamples thereof include methyl, tert-butyl, tert-octyl, 2-ethylhexyl,cyclohexyl, n-hexadecyl, 3-dodecyloxypropyl and3-(2′,4′-di-tert-pentylphenoxy)propyl.

The aryl group represented by R₂ in formula (2) is preferably an arylgroup having a carbon number of 6 to 60, more preferably a carbon numberof 6 to 50, still more preferably a carbon number of 6 to 40. Specificexamples thereof include phenyl, 1-naphthyl, p-tolyl, o-tolyl,4-methoxyphenyl, 4-hexadecyloxyphenyl, 3-pentadecylphenyl,2,4-di-tert-pentylphenyl, 8-quinolyl and5-(1-dodecyloxycarbonylethoxycarbonyl)-2-chlorophenyl.

The heteroaryl group represented by R₂ in formula (2) is preferably a 5-to 8-membered heteroaryl group containing at least one heteroatomselected from among N, S, O and Se. Specific examples thereof include4-pyridyl, 2-furyl, 2-pyrrole, 2-thiazolyl, 3-thiazolyl, 2-oxazolyl,2-imidazolyl, triazolyl, tetrazolyl, benzotriazolyl, morpholinyl, and anacyl group (e.g., acetyl, butanoyl, dodecanoyl, benzoyl).

The sulfonyl group represented by R₂ in formula (2) is preferably asulfonyl group having a carbon number of 1 to 60, more preferably acarbon number of 1 to 50, still more preferably a carbon number of 1 to40. Specific examples thereof include phenylslufonyl, methylsulfonyl,ethylsulfonyl and propylsulfonyl.

R₁ and R₂ may be either the same or different, and R₁ and R₂ may combinewith each other to form a ring.

From the standpoint that high antistatic property, light resistance anddurability can be obtained while maintaining the strength andtransparency of the coating film, the compound represented by formula(2) is preferably at least one compound selected from the groupconsisting of a hydroxamic acid compound and a hydroxyamine compound.

-Hydroxamic Acid Compound-

The hydroxamic acid compound is preferably a compound represented by thefollowing formula (2-2).

In formula (2-2), each of R₂₁ and R₂₂ is independently a hydrogen atomor a substituted or unsubstituted alkyl, aryl, heteroaryl, alkoxy oraryloxy group, preferably a substituted or unsubstituted alkyl or arylgroup, more preferably a substituted or unsubstituted alkyl or phenylgroup. These groups each may be unsubstituted or may have a substituent.

The alkyl group represented by R₂₁ in formula (2-2) is preferably analkyl group having a carbon number of 1 to 60, more preferably an alkylgroup having a carbon number of 1 to 50, still more preferably an alkylgroup having a carbon number of 1 to 40. The alkyl group may be linear,branched or cyclic but is preferably a linear or branched alkyl group.

The alkyl group represented by R₂₁ in formula (2-2) may be furthersubstituted, and the substituent is preferably a polyvinyl group, apolypropylene group, a polystyrene group, a fluorine atom, a chlorineatom, a sulfo group, a phosphonic group, a carboxy group, analkoxycarbonyl group or an amino or ammonium group which may besubstituted, more preferably a polyvinyl group, a polypropylene group, apolystyrene group, a fluorine atom, a sulfo group, a phosphonic group, acarboxy group, an alkoxycarbonyl group, an amino group or an ammoniumgroup, still more preferably a sulfo group, a phosphonic group or acarboxy group. In the polyvinyl group, polypropylene group andpolystyrene group as the substituent, the number of repeating units ispreferably from 10 to 100,000, more preferably from 10 to 10,000, and inview of viscosity, still more preferably from 10 to 5,000.

The aryl group represented by R₂₁ in formula (2-2) is preferably an arylgroup having a carbon number of 6 to 60, more preferably an aryl grouphaving a carbon number of 6 to 30, still more preferably a phenyl groupor a naphthyl group, yet still more preferably a phenyl group.

The aryl group represented by R₂₁ in formula (2-2) may be furthersubstituted, and the substituent is preferably an alkyl group, a halogenatom, a sulfo group or a salt thereof, a phosphonic group, a carboxygroup, a halogen atom, a hydroxy group, a heteroaryl group or an aminogroup which may be substituted, more preferably an alkyl group, ahalogen atom, a sulfo group or a salt thereof, a phosphonic group, acarboxy group, a halogen atom or a hydroxy group, still more preferablyan alkyl group, a carboxy group or a hydroxy group. The alkyl group asthe substituent of the aryl group represented by R₂₁ preferably has acarbon number of 1 to 60, more preferably a carbon number of 1 to 40,still more preferably a carbon number of 1 to 30.

The number of substituents when R₂₁ is a phenyl group is preferably from0 to 5, more preferably from 0 to 4. The substitution position of thesubstituent when R₂₁ is a phenyl group is not particularly limited butis preferably a meta-position or a para-position with respect to thecarbonyl group in formula (2-2).

The heteroaryl group represented by R₂₁ in formula (2-2) has the samemeaning as the heteroaryl group represented by R₁ in formula (2), andits preferred range is also the same.

The alkoxyl group represented by R₂₁ in formula (2-2) preferably has acarbon number of 1 to 60, more preferably a carbon number of 1 to 50,and still more preferably a carbon number of 1 to 40. The alkoxyl grouprepresented by R₂₁ in formula (2-2) may be further substituted, and thesubstituent includes a hydroxy group, a phosphonic group, a sulfo groupand a carboxy group.

The aryloxy group represented by R₂₁ in formula (2-2) is preferably anaryloxy group having a carbon number of 6 to 60, more preferably anaryloxy group having a carbon number of 6 to 50, still more preferably aphenyloxy group or a naphthyloxy group. The aryloxy group represented byR₂₁ in formula (2-2) may be further substituted, and the substituent ispreferably a sulfo group, a phosphonic group, a carboxy group, a saltthereof, or an amino, alkyl, hydroxy, aryl or heteroaryl group which maybe substituted, more preferably a sulfo group, a phosphonic group, acarboxy group, an amino group, an ammonium group, a hydroxy group or analkyl group.

R₂₂ in formula (2-2) is preferably a hydrogen atom, an alkyl group, anaryl group or a heteroaryl group, more preferably a hydrogen atom, analkyl group or an aryl group, still more preferably a hydrogen atom, analkyl group or a phenyl group.

The alkyl group represented by R₂₂ in formula (2-2) is preferably analkyl group having a carbon number of 1 to 60, more preferably an alkylgroup having a carbon number of 1 to 50, and still more preferably analkyl group having a carbon number of 1 to 40. The alkyl grouprepresented by R₂₂ in formula (2-2) may be further substituted, and thesubstituent includes a hydroxy group, a phosphonic group, a sulfo groupand a carboxy group.

The aryl group represented by R₂₂ in formula (2-2) is preferably an arylgroup having a carbon number of 6 to 60, more preferably an aryl grouphaving a carbon number of 6 to 50, still more preferably a phenyl groupor a naphthyl group.

The aryl group represented by R₂₂ in formula (2-2) may be furthersubstituted, and the substituent is preferably a sulfo group, aphosphonic group, a carboxy group, a salt thereof or an amino, alkyl,hydroxy, aryl or heteroaryl group which may be substituted, morepreferably a sulfo group, a phosphonic group, a carboxy group, an aminogroup, an ammonium group, a hydroxy group or an alkyl group. The alkylgroup as the substituent of the aryl group represented by R₂₂ preferablyhas a carbon number of 1 to 60, more preferably a carbon number of 1 to50, still more preferably a carbon number of 1 to 40.

The number of substituents when R₂₂ in formula (2-2) is a phenyl groupis preferably from 0 to 4, more preferably from 0 to 3. The substitutionposition of the substituent when R₂₂ in formula (2-2) is a phenyl groupis not particularly limited but is preferably a meta-position or apara-position with respect to the carbonyl group in formula (2-2).

The heteroaryl group represented by R₂₂ in formula (2-2) has the samemeaning as the heteroaryl group represented by R₂ in formula (1), andits preferred range is also the same.

-Hydroxyamine Compound-

The hydroxyamine compound is preferably a compound represented by thefollowing formula (2-3).

In formula (2-3), each of R₃₁ and R₃₂ is independently a hydrogen atomor a substituted or unsubstituted alkyl, aryl, heteroaryl, alkoxy oraryloxy group, preferably a hydrogen atom or a substituted orunsubstituted alkyl or aryl group, more preferably a hydrogen atom or asubstituted or unsubstituted alkyl or phenyl group.

The alkyl group represented by R₃₁ or R₃₂ in formula (2-3) is preferablyan alkyl group having a carbon number of 1 to 60, more preferably analkyl group having a carbon number of 1 to 50, still more preferably analkyl group having a carbon number of 1 to 40. R₃₁ and R₃₂ may combinewith each other to form a ring.

The alkyl group represented by R₃₁ or R₃₂ in formula (2-3) may befurther substituted, and the substituent is preferably a hydroxy group,a sulfo group, a phosphonic group, a carboxy group, a polyvinyl group, apolypropylene group or a polystyrene group, more preferably a hydroxygroup, a sulfo group, a phosphonic group, a carboxy group, an aminogroup, an ammonium group, a polyvinyl group, a polypropylene group or apolystyrene group, still more preferably a hydroxy group, a sulfo group,a phosphonic group or a carboxy group. In the polyvinyl group,polypropylene group and polystyrene group as the substituent, the numberof repeating units is preferably from 10 to 100,000, more preferablyfrom 10 to 10,000, and in view of viscosity, still more preferably from10 to 5,000.

The aryl group represented by R₃₁ or R₃₂ in formula (2-3) is preferablyan aryl group having a carbon number of 6 to 60, more preferably an arylgroup having a carbon number of 6 to 50, still more preferably a phenylgroup or a naphthyl group.

The aryl group represented by R₃₁ or R₃₂ in formula (2-3) may be furthersubstituted, and the substituent is preferably a sulfo group, aphosphonic group, a carboxy group, an alkyl group, an aryl group, ahydroxy group, or an amino group which may be substituted, morepreferably a sulfo group, a phosphonic group, a carboxy group, an alkylgroup or a hydroxy group, still more preferably a sulfo group, a carboxygroup or a hydroxy group. The alkyl group as the substituent of the arylgroup represented by R₃₁ or R₃₂ preferably has a carbon number of 1 to60, more preferably a carbon number of 1 to 50, still more preferably acarbon number of 1 to 40.

The number of substituents when R₃₁ is a phenyl group is preferably from0 to 5, more preferably from 0 to 4. The substitution position of thesubstituent when R₃₁ or R₃₂ is a phenyl group is not particularlylimited but is preferably a para-position with respect to the nitrogenatom in formula (2-3).

The heteroaryl group represented by R₃₁ or R₃₂ in formula (2-3) has thesame meaning as the heteroaryl group represented by R₂ in formula (1),and its preferred range is also the same.

The alkoxyl group represented by R₃₁ or R₃₂ in formula (2-3) preferablyhas a carbon number of 1 to 60, more preferably a carbon number of 1 to50, still more preferably a carbon number of 1 to 40. The alkoxyl grouprepresented by R₃₂ in formula (2-3) may be further substituted, and thesubstituent includes a hydroxy group, a phosphonic group, a sulfo groupand a carboxy group.

The aryloxy group represented by R₃₁ or R₃₂ in formula (2-3) ispreferably an aryloxy group having a carbon number of 6 to 60, morepreferably an aryloxy group having a carbon number of 6 to 50, stillmore preferably a phenyloxy group or a naphthyloxy group. The aryloxygroup represented by R₃₂ in formula (2-3) may be further substituted,and the substituent is preferably a sulfo group, a phosphonic group, acarboxy group, a salt thereof, an amino group which may be substituted,an alkyl group, a hydroxy group, an aryl group or a heteroaryl group,more preferably a sulfo group, a phosphonic group, a carboxy group, anamino group, an ammonium group, a hydroxy group or an alkyl group.

R₃₁ and R₃₂ may be the same or different, but in view of easyavailability, R₃₁ and R₃₂ are preferably the same.

Specific examples of the compound represented by formula (2) for use inthe present invention are illustrated below, but the compoundrepresented by formula (2) of the present invention is not limited tothese specific examples.

Hydroxamic Acid Compound:

HX-1 R₁ = CH₃, R₂ = H HX-2 R₁ = C₂H₅, R₂ = H HX-3 R₁ = C₃H₇, R₂ = H HX-4R₁ = C₄H₉, R₂ = H HX-5 R₁ = C₇H₁₅, R₂ = H HX-6 R₁ = C₉H₁₉, R₂ = H HX-7R₁ = C₁₅H₃₁, R₂ = H HX-8 R₁ = CH₃, R₂ = CH₃ HX-9 R₁ = C₇H₁₅, R₂ = CH₃HX-10 R₁ = C₉H₁₉, R₂ = CH₃ HX-11 R₁ = C₁₅H₃₁, R₂ = C₂H₅ HX-12 R₁ =CF₂CF₂CF₃, R₂ = CH₃ HX-13 R₁ = (CH₂)₂CO₂CH₃, R₂ = CH₃ HX-14 R₁ =CH₂N(CH₃)₂, R₂ = CH₃ HX-15 R₁ = (CH₂)₃N⁺(CH₃)₃•Br⁻, R₂ = CH₃ HX-16 R₁ =(CH₂)₃SO₃H, R₂ = CH₃ HX-17 R₁ = (CH₂)₃COOH, R₂ = CH₃ HX-18 R₁ =(CH₂)₃PO(OH)₂, R₂ = CH₃

HX-19 V₁ = H, V₂ = H, R₂ = H HX-20 V₁ = H, V₂ = H, R₂ = CH₃ HX-21 V₁ =H, V₂ = H, R₂ = Ph HX-22 V₁ = Cl, V₂ = H, R₂ = CH₃ HX-23 V₁ = CH₃, V₂ =H, R₂ = H HX-24 V₁ = H, V₂ = OH, R₂ = C₂H₅ HX-25 V₁ = SO₃H, V₂ = H, R₂ =CH₃ HX-26 V₁ = SO₃Na, V₂ = H, R₂ = CH₃ HX-27 V₁ = COOH, V₂ = H, R₂ = CH₃HX-28 V₁ = PO(OH)₂, V₂ = H, R₂ = CH₃

HX-29 R₁ = (CH₂)₄, R₂ = H, R₃ = H HX-30 R₁= (CH₂)₄, R₂ = CH₃, R₃ = HHX-31 R₁ = (CH₂)₆, R₂ = CH₃, R₃ = CH₃ HX-32

HX-33

HX-34

HX-35

HX-36

HX-37

HX-38

HX-39

HX-40

Hydroxyamine Compound:

HA-1 R₁ = R₂ = CH₃ HA-2 R₁ = R₂ = H HA-3 R₁ = Ph, R₂ = Ph HA-4

HA-5

HA-6 R₁ = R₂ = C₂H₅ HA-7 R₁ = R₂ = C₇H₁₅ HA-8 R₁ = R₂ = (CH₂)₆SO₃H HA-9R₁ = R₂ = (CH₂)₆OH HA-10 R₁ = R₂ = (CH₂)₄COOH HA-11 R₁ = R₂ =(CH₂)₄PO(OH)₂ HA-12 R₁ = C₆H₁₃, R₂ = C₂H₅

HA-13 V₁ = H, R₂ = CH₃ HA-14 V₁ = CH₃, R₂ = CH₃ HA-15 V₁ = OH, R₂ = PhHA-16 V₁ = SO₃H, R₂ = C₆H₄—4-SO₃H HA-17 V₁ = COOH, R₂ = H HA-18 V₁ =PO(OH)₂, R₂ = C₂H₅

HA-19 R₁ = (CH₂)₄, R₂ = CH₃, R₃ = H HA-20 R₁ = (CH₂)₄, R₂ = CH₃, R₃ =CH₃ HA-21 R₁ = (CH₂)₆, R₂ = C₆H₅, R₃ = CH₃ HA-22

HA-23

HA-24

HA-25

HA-26

HA-27

HA-28

The compound represented by formula (2) can be synthesized by a knownmethod. More specifically, a method of reacting a hydroxylamine with acarboxylic acid halide or a carboxylic acid ester to synthesize thecompound is suitably used. Also, some of the compounds represented byformula (2) are available as a commercial product, and examples thereofinclude acetohydroxamic acid (produced by Tokyo Chemical Industry Co.,Ltd.), N-methylfurohydroxamic acid (produced by Tokyo Chemical IndustryCo., Ltd.), benzohydroxamic acid (produced by Tokyo Chemical IndustryCo., Ltd.) and octanohydroxamic acid (produced by Tokyo ChemicalIndustry Co., Ltd.).

The ratio between the compound represented by formula (2) of the presentinvention and the electrically conductive polymer may be any ratio butfrom the standpoint of satisfying both high electrical conductivity andhigh durability, the ratio (compound represented by formula (2):electrically conductive polymer) is, in terms of mass ratio, preferablyfrom 0.01:1.0 to 100:1, more preferably from 0.05:1.0 to 10:1, stillmore preferably from 0.05:1.0 to 5.0:1.0.

The method for adding the compound represented by formula (2) may be anymethod. A method of mixing a liquid dispersion containing theelectrically conductive polymer and a solution having dissolved thereinthe compound represented by formula (2) is preferred. This is describedin detail later.

<Compound (3)>

The compound (3) contains a trivalent phosphorus compound. The trivalentphosphorus compound causes no aggregation even when coexists with theelectrically conductive polymer of the present invention. Therefore, anantistatic layer formed using a composition containing a trivalentphosphorus compound and the electrically conductive polymer exhibitshigh transparency and good antistatic property and moreover, isexcellent in the light resistance. Incidentally, while a polyphosphoricacid when added causes aggregation of the electrically conductivepolymer, aggregation is not caused by a trivalent phosphorus compound.The reason therefor is presumed because the pH of the electricallyconductive polymer composition does not change even when a trivalentphosphorus compound is added. However, the present invention is notlimited by such a presumption.

The trivalent phosphorus compound is preferably a compound representedby the following formula (I), (II), (III) or (IV).

In formulae (I), (II), (III) and (IV), R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸,R⁹, R¹⁰, R¹¹ and R¹² each independently represents a hydrogen atom or asubstituted or unsubstituted alkyl, aryl or heteroaryl group and ispreferably a substituted or unsubstituted alkyl, aryl or heteroarylgroup in terms of giving high light resistance, and more preferably asubstituted or unsubstituted alkyl group in view of solubility.

R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹ and R¹² may combine witheach other to form a ring.

The alkyl group, aryl group and heteroaryl group represented by R¹ toR¹² may have a substituent. Examples of the substituent include thesubstituent group V.

The alkyl group represented by R¹ to R¹² is preferably a substituted orunsubstituted alkyl group having a carbon number of 1 to 60, morepreferably a carbon number of 1 to 50, still more preferably a carbonnumber of 1 to 40.

The alkyl group represented by R¹ to R¹² may be linear, branched orcyclic, but in view of cost and solubility, a linear or branched alkylgroup is preferred.

As for the substituent of the alkyl group represented by R¹ to R¹²,among the substituent group V, an alkyl group, an aryl group, an alkoxygroup, a halogen atom, a hydroxy group, a substituted or unsubstitutedamino group, a carboxyl group, a phosphoric acid group and a sulfo groupare preferred; an alkyl group, an alkoxy group, a hydroxy group, asubstituted amino group, a carboxyl group, a phosphoric acid group and asulfo group are more preferred; and a hydroxy group, a substituted aminogroup, a phosphoric acid group and a sulfo group are still morepreferred.

Specific examples of the alkyl group represented by R¹ to R¹² includemethyl, ethyl, propyl, butyl, pentyl, octyl, 2-ethylhexyl, cyclohexyl,hexadecyl, 3-dodecyloxypropyl and 3-(2′,4′-di-tert-pentylphenoxy)propyl.

The aryl group represented by R¹ to R¹² is preferably a substituted orunsubstituted aryl group having a carbon number of 6 to 60, morepreferably a carbon number of 6 to 50, still more preferably a carbonnumber of 6 to 40.

As for the substituent of the aryl group represented by R¹ to R¹², amongthe substituent group V, an alkyl group, an aryl group, an alkoxy group,a halogen atom, a hydroxy group, a substituted or unsubstituted aminogroup, a carboxyl group, a phosphoric acid group and a sulfo group arepreferred; an alkyl group, an alkoxy group, a hydroxy group, asubstituted amino group, a carboxyl group, a phosphoric acid group and asulfo group are more preferred; and a hydroxy group, a substituted aminogroup, a phosphoric acid group and a sulfo group are still morepreferred.

In the case where the aryl group represented by R¹ to R¹² is a phenylgroup, the substitution position of the substituent on the phenyl groupis not particularly limited, but when the number of substituents is 1,the phenyl group preferably has the substituent at the 4-position fromthe standpoint of giving high light resistance, and when the number ofsubstituents is 2, the phenyl group preferably has the substituents atthe 2,6-position and the 3,5-position.

Specific examples of the aryl group represented by R¹ to R¹² includephenyl, 1-naphthyl, p-tolyl, o-tolyl, 4-methoxyphenyl,4-hexadecyloxyphenyl, 3-pentadecylphenyl, 2,4-di-tert-pentylphenyl,8-quinolyl and 5-(1-dodecyloxycarbonylethoxycarbonyl)-2-chlorophenyl.

The heteroaryl group represented by R¹ to R¹² is preferably a 5- to8-membered heteroaryl group containing at least one heteroatom selectedfrom N, S, O and Se. Specific examples thereof include 4-pyridyl,2-furyl, 2-pyrrole, 2-thiazolyl, 3-thiazolyl, 2-oxazolyl, 2-imidazolyl,triazolyl, tetrazolyl, benzotriazolyl, 2-quinolyl and 3-quinolyl.

In view of solubility, the trivalent phosphorus compound is preferably acompound represented by formula (I). R¹, R² and R³ in formula (I) may bethe same or different and are preferably the same from the standpoint ofcost and easy availability. Each of R¹, R² and R³ in formula (I) ispreferably a substituted or unsubstituted alkyl group in view ofsolubility, more preferably an alkyl group having no substituent fromthe standpoint of cost.

The trivalent phosphorus compound may be a salt compound. The functionalgroup forming such a salt includes an ammonium group and a sulfoniumgroup. The counter ion includes an anionic counter ion (e.g., Cl⁻, Br⁻,I⁻, ClO₄ ⁻, PF₆ ⁻, AsF₆ ⁻, SbP₆ ⁻, BF₄ ⁻, various sulfonate anions) foran ammonium group and a cationic counter ion (e.g., Na⁺, K⁺, Mg²⁺) for asulfonium group.

Specific examples of the trivalent phosphorus compound for use in thepresent invention are illustrated below, but the present invention isnot limited to these specific examples.

P

OR)₃ PA-1 R = CH₃ PA-2 R = C₂H₅ PA-3 R = n-C₃H₇ PA-4 R = n-C₄H₉ PA-5 R =t-C₄H₉ PA-6 R = n-C₅H₁₁ PA-7 R = n-C₇H₁₄COOH PA-8 R = (CH₂)₂Cl PA-9 R =n-C₁₁H₂₂OH PA-10

PA-11

PA-12

PA-13

PA-14

 indicates a bonding position.

V1 V2 V3 V4 V5 PA-15 H H H H H PA-16 H H CH₃ H H PA-17 H H n-C₉H₁₉ H HPA-18 H H OCH₃ H H PA-19 H Cl Cl H H PA-20 CH₃ H H H CH₃ PA-21 CH₃ H CH₃H CH₃ PA-22 H H Ph H H PA-23 H OH OH OH H PA-24 H H NH₂ H H PA-25 H HCOOH H H PA-26 H H SO₃H H H PA-27 H H PO(OH)₂ H H PA-28 CH₃ CH₃ CH₃ CH₃CH₃

R¹O—P

OR²)₂ PA-32 R¹ = CH₃, R² = C₂H₅ PA-33 R¹ = Ph, R² = C₂H₅ PA-34 R¹ =n-C₁₃H₂₇, R² = C₂H₅ PA-35

PA-36 R = n-C₁₈H₃₇ PA-37 R = n-C₁₀H₂₁

PA-38 R₁ = (CH₂)₄, R₂ = CH₃, R₃ = CH₃ PA-39 R₁ = (CH₂)₄, R₂ = C₆H₅, R₃ =C₆H₅ PA-40

P

OR)₃ PA-41 R = n-C₇H₁₄N⁺Et₃ Cl⁻ PA-42

PA-43

P

R)₃ PB-1 R = CH₃ PB-2 R = C₂H₅ PB-3 R = n-C₃H₇ PB-4 R = n-C₄H₉ PB-5 R =t-C₄H₉ PB-6 R = n-C₅H₁₁ PB-7 R = n-C₇H₁₄COOH PB-8 R = n-C₉H₁₉ PB-9 R =n-C₁₁H₂₂OH PB-10

PB-11

PB-12

PB-13

PB-14

 indicates a bonding position.

V1 V2 V3 V4 V5 PB-15 H H H H H PB-16 H H CH₃ H H PB-17 H H n-C₉H₁₉ H HPB-18 H H OCH₃ H H PB-19 H Cl Cl H H PB-20 CH₃ H H H CH₃ PB-21 CH₃ H CH₃H CH₃ PB-22 H H Ph H H PB-23 H OH OH OH H PB-24 H H NH₂ H H PB-25 H HCOOH H H PB-26 H H SO₃H H H PB-27 H H PO(OH)₂ H H PB-28 CH₃ CH₃ CH₃ CH₃CH₃

R¹—P

R²)₂ PB-32 R¹ = CH₃, R² = C₂H₅ PB-33 R¹ = Ph, R² = C₂H₅ PB-34 R¹ =n-C₁₃H₂₇, R² = C₂H₅ PB-35

PB-36

PB-37

PB-38 R₁ = (CH₂)₄, R₂ = CH₃, R₃ = CH₃ PB-39 R₁= (CH₂)₄, R₂ = C₆H₅, R₃ =C₆H₅ PB-40

P

R)₃ PB-41 R = n-C₇H₁₄N⁺Et₃ Cl⁻ PB-42

PB-43

R¹O—P

R²)₂ PC-1 R¹ = CH₃, R² = CH₃ PC-2 R¹ = C₂H₅, R² = C₂H₅ PC-3 R¹ = C₅H₁₁,R² = C₄H₉ PC-4 R¹ = C₂H₄OH, R² = C₂H₅ PC-5 R¹ = C₂H₄SO₃H, R² = Ph PC-6R¹ = Ph, R² = Ph PC-7 R¹ = Ph, R² = C₆H₄-4-OH PC-8 R¹ = Ph, R² =C₆H₄-4-PO(OH)₂ R¹—P

OR²)₂ PD-1 R¹ = CH₃, R² = CH₃ PD-2 R¹ = C₂H₅, R² = C₂H₅ PD-3 R¹ = C₅H₁₁,R² = C₄H₉ PD-4 R¹ = C₂H₄OH, R² = C₂H₅ PD-5 R¹ = C₂H₄SO₃H, R² = Ph PD-6R¹ = Ph, R² = Ph PD-7 R¹ = Ph, R² = C₆H₄-4-OH PD-8 R¹ = Ph, R² =C₆H₄-4-PO(OH)₂

The trivalent phosphorus compound can be synthesized by a known method.More specifically, the methods described in G. M. Kosolapoff and L.Maier (compilers), Organic Phosphorus Compounds, John Wiley & Sons Inc.(1973) and JPA-2004-256456 are preferably used. Also, some trivalentphosphorus compounds are available as a commercial product, and examplesthereof include Phosphorous Acid Tris(2-chloroethyl)Ester (produced byTokyo Chemical Industry Co., Ltd.), Tris(2-ethylhexyl)Phosphite(produced by Tokyo Chemical Industry Co., Ltd.), Trihexyl Phosphite(produced by Tokyo Chemical Industry Co., Ltd.), Triisodecyl Phosphite(produced by Tokyo Chemical Industry Co., Ltd.), Trimethyl Phosphite(produced by Tokyo Chemical Industry Co., Ltd.), Tri-n-octadecylPhosphite (produced by Tokyo Chemical Industry Co., Ltd.),Trimethylolpropane Phosphite (produced by Tokyo Chemical Industry Co.,Ltd.), 1,2-Bis(dimethylphosphino)ethane (produced by Tokyo ChemicalIndustry Co., Ltd.), Tributylphosphine (produced by Tokyo ChemicalIndustry Co., Ltd.), Tri-n-octylphosphine (produced by Tokyo ChemicalIndustry Co., Ltd.), Trihexylphosphine (produced by Tokyo ChemicalIndustry Co., Ltd.), Tricyclohexylphosphine (produced by Tokyo ChemicalIndustry Co., Ltd.) and Tris(2-carboxyethyl)phosphine Hydrochloride(produced by Tokyo Chemical Industry Co., Ltd.).

The blending ratio between the trivalent phosphorus compound and theelectrically conductive polymer may be any ratio, but from thestandpoint of satisfying both high electrical conductivity and highdurability, the ratio (trivalent phosphorus compound:electricallyconductive polymer) is, in terms of mass ratio, preferably from 0.01:1.0to 100:1, more preferably from 0.05:1.0 to 10:1, still more preferablyfrom 0.05:1.0 to 5.0:1.0.

The method for adding the trivalent phosphorus compound may be anymethod. A method of mixing a liquid dispersion containing theelectrically conductive polymer and a solution having dissolved thereinthe trivalent phosphorus compound is preferred. This is described indetail later.

The compounds represented by compounds (1) to (3) are preferably used incombination so as to enhance the light resistance and heat resistance.In particular, a combination use of the compound (1) and the compound(2), and a combination use of the compound (1) and the compound (3) arepreferred.

In the case of using the compound (1) and the compound (2) incombination, the blending ratio between the compound (1) and thecompound (2) may be any ratio, but the ratio (compound (1):compound (2))is preferably from 10:1 to 1:10, more preferably from 5:1 to 1:1.

In the case of using the compound (1) and the compound (3) incombination, the blending ratio between the compound (1) and thecompound (3) may be any ratio, but the ratio (compound (1):compound (3))is preferably from 10:1 to 1:10, more preferably from 5:1 to 1:1.

(Other Additives)

-Dopant-

From the standpoint that the dispersibility in a solvent at thepreparation of a composition for forming the antistatic layer of thepresent invention is improved, the antistatic layer preferably containsat least one kind of a dopant. The antistatic layer is preferably formedby coating as described later, and in view of the production, it isimportant to obtain a liquid dispersion (composition) having gooddispersibility. Incidentally, the “dopant” as used in the presentinvention means an additive having an action of changing the electricalconductivity of the electrically conductive polymer. This dopantincludes an electron-accepting (acceptor) dopant and anelectron-donating (donor) dopant.

Examples of the electron-accepting (acceptor) dopant include a halogen(Cl₂, Br₂, I₂, ICl, ICl₃, IBr, IF), a Lewis acid (PF₅, AsF₅, SbF₅, BF₃,BCl₃, BBr₃, SO₃), a protic acid (e.g., HF, HCl, HNO₃, H₂SO₄, HClO₄,FSO₃H, CISO₃H, CF₃SO₃H, various organic acids, amino acids), atransition metal compound (FeCl₃, FeOCl, TiCl₄, ZrCl₄, HfCl₄, NbF₅,NbCl₅, TaCl₅, MoF₅, MoCl₅, WF₆, WCl₆, UF₆, LnCl₃ (Ln is a lanthanidesuch as La, Ce, Pr, Nd and Sm), an electrolyte anion (Cl⁻, Br⁻, I⁻, ClO₄⁻, PF₆ ⁻, AsF₆ ⁻, SbF₆ ⁻, various sulfonate anions), O₂, XeOF₄, (NO₂⁻,BF₄ ⁺)(SbF₆ ⁻), (NO₂ ⁺)(SbCl₆ ⁻), (NO₂ ⁺)(BF₄ ⁻), FSO₂OOSO₂F, AgClO₄,H₂IrCl₆ and La(NO₃)₃.6H₂O.

Examples of the electron-donating (donor) dopant include an alkali metal(Li, Na, K, Rb, Cs), an alkaline earth metal (Ca, Sr, Ba), a lanthanides(e.g., Eu), and others (R₄N⁺, R₄P⁺, R₄As⁺, R₃S⁺, acetylcholine, whereinR is a substituted or unsubstituted hydrocarbon group).

Examples of the combination of the dopant and the electricallyconductive polymer include:

(A) polyacetylene with I₂, AsF₅, FeCl₃ or the like;

(B) poly(p-phenylene) with AsF₅, K, AsF₆ ⁻ or the like;

(C) polypyrrole with ClO₄ ⁻ or the like;

(D) polythiophenes with ClO₄ ⁻, a sulfonic acid compound, particularlypolystyrenesulfonic acid, a nitrosonium salt, an aminium salt, quinonesor the like;

(E) polyisothianaphthene with I₂ or the like;

(F) poly(p-phenylene sulfide) with AsF₅;

(G) poly(p-phenylene oxide) with AsF₅;

(H) polyaniline with HCl, a dodecylbenzenesulfonic acid or the like;

(I) poly(p-phenylenevinylene) with H₂SO₄ or the like;

(J) polythiophenylenevinylene with I₂ or the like;

(K) nickel phthalocyanine with I₂ or the like.

Among these combinations, the combinations (D) and (H) are preferred;the combination of polythiophenes (polythiophene and its derivative)with a sulfonic acid compound is more preferred in view of highstability of the doped state; and the combination of polythiophenes witha polystyrenesulfonic acid is still more preferred from the standpointthat preparation of a water dispersion is possible and an electricallyconductive thin film can be easily prepared by coating.

The ratio between the electrically conductive polymer and the dopant maybe any ratio, but from the standpoint of satisfying both the stabilityof doped state and the electrical conductivity, the ratio (electricallyconductive polymer:dopant) is, in terms of mass ratio, preferably from1.0:0.0000001 to 1.0:10, more preferably from 1.0:0.00001 to 1.0:1.0,still more preferably from 1.0:0.0001 to 1.0:0.5.

On the other hand, in order to enhance the dispersibility of theelectrically conductive polymer, an ion-conductive polymer prepared bydoping an electrolyte into a polymer chain may be used. Examples of thepolymer chain include a polyether (e.g., polyethylene oxide,polypropylene oxide), a polyester (e.g., polyethylene succinate,poly-β-propiolactone), a polyamine (e.g., polyethyleneimine), and apolysulfide (e.g., polyalkylene sulfide). Examples of the electrolytedoped include various alkali metal salts.

Examples of the alkali metal ion constituting the alkali metal saltinclude Li⁺, Na⁺, K⁺, Rb⁺ and Cs⁺, and examples of the anion forming thecounter salt include F⁻, Cl⁻, Br⁻, I⁻, NO₃ ⁻, SCN⁻, ClO₄ ⁻, CF₃SO₃ ⁻,BF₄ ⁻, AsF₆ ⁻ and BPh₄ ⁻.

Examples of the combination of the polymer chain and the alkali metalsalt include a combination of polyethylene oxide with LiCF₃SO₃, LiClO₄or the like, a combination of polyethylene succinate with LiClO₄, LiBF₄,poly-β-propiolactone, LiClO₄ or the like, a combination ofpolyethyleneimine with NaCF₃SO₃, LiBF₄ or the like, and a combination ofpolyalkylene sulfide with AgNO₃ or the like.

-Photopolymerization Initiator-

The composition for forming the antistatic layer in the presentinvention preferably contains a photopolymerization initiator. Examplesof the photopolymerization initiator include acetophenones, benzoins,benzophenones, phosphine oxides, ketals, anthraquinones, thioxanthones,azo compounds, peroxides, 2,3-dialkyldione compounds, disulfidecompounds, fluoroamine compounds, aromatic sulfoniums, lophine dimers,onium salts, borate salts, active esters, active halogens, inorganiccomplexes and coumarins. Specific examples, preferred embodiments andcommercial products of the photopolymerization initiator are describedin JPA-2009-098658, paragraphs [0133] to [0151], and these can besuitably used also in the present invention.

Various examples are also described in Saishin UV Koka Gijutsu (LatestUV Curing Technology), Technical Information Institute Co., Ltd., page159 (1991), and Kiyomi Kato, Shigaisen Koka System (Ultraviolet CuringSystem), Sogo Gijutsu Center, pp. 65-148 (1989), and these are useful inthe present invention.

(Surfactant)

Various surfactants are preferably used in the antistatic layer of thepresent invention. In general, a surfactant is added to suppress thethickness unevenness or the like resulting from variation in drying dueto local distribution of the drying air. In the present invention, inaddition to this effect, it has been found that surface unevenness ofthe antistatic layer or repellency of the coated material, which isestimated to be attributable to the compatibility of materials, can beimproved. In particular, when the component (C) is added so as toimprove the durability (light resistance, heat resistance, wet heatresistance), the coating film surface is sometimes roughened, but thisroughening can be suppressed by using a surfactant in combination andboth electrical conductivity and durability can be satisfied at a highlevel.

Specifically, the surfactant is preferably a fluorine-containingsurfactant or a silicone-containing surfactant. Also, the surfactant ispreferably an oligomer or a polymer rather than a low molecularcompound.

When a surfactant is added, the surfactant swiftly moves and is unevenlydistributed to the surface of the coated liquid film, and the surfactantremains unevenly distributed to the surface after drying, as a result,the surface energy of the antistatic layer to which the surfactant isadded decreases by the effect of the surfactant. From the standpoint ofpreventing thickness non-uniformity, repellency or unevenness of theantistatic layer, the surface energy of the film is preferably lower.

The surface energy (γs^(v), unit: mJ/m²) of the layer can beexperimentally determined using pure water H₂O and methylene iodideCH₂I₂ on the layer by referring to D. K. Owens, J. Appl. Polym. Sci.,Vol. 13, page 1741 (1969). At this time, assuming that the contactangles for pure water and methylene iodide are θ_(H2O) and θ_(CH2I2),respectively, γs^(d) and γs^(h) are obtained according to the followingsimultaneous equations (1) and (2) and from the value γs^(v)(=γs^(d)+γs^(h)) as the sum thereof, the energy-equivalent value (avalue obtained by converting the mN/m unit into the mJ/m² unit) ofsurface tension of the antiglare layer is determined and defined as thesurface energy. Before the measurement, the sample needs to be subjectedto humidity conditioning under predetermined temperature and humidityconditions for a fixed time or more. The temperature here is preferablyfrom 20 to 27° C., the humidity is preferably from 50 to 65 RH %, andthe humidity conditioning time is preferably 2 hours or more.1+cos θ_(H2O)=2√γs ^(d)(√γ_(H2O) _(d) /γ_(H2O) _(v) )+2√γs^(h)(√γ_(H2O)_(h) /γ_(H2O) _(v) )  (1)1+cos θ_(CH2I2)=2√γs ^(d)(√γ_(CH2I2) _(d) /γ_(CH2I2) _(v))+2√γs^(h)(√γ_(CH2I2) _(h) /γ_(CH2I2) _(v) )  (2)wherein γ_(H2O) _(d) =21.8°, γ_(H2O) _(h) =51.0°, γ_(H2O) _(v) =72.8°,γ_(CH2I2) _(d) =49.5°, γ_(CH2I2) _(h) =1.3° and γ_(CH2I2) _(v) =50.8°.

The surface energy of the antistatic layer is preferably 45 mJ/m² orless, more preferably from 20 to 45 mJ/m², still more preferably from 20to 40 mJ/m². By setting the surface energy of the layer to 45 mJ/m² orless, an effect such as thickness uniformization or improved repellencyon the antistatic layer can be obtained. However, in the case of furthercoating an upper layer such as low refractive index layer on the layerto which the surfactant is added, the surfactant is preferably asurfactant capable of dissolving out and moving into the upper layer,and the surface energy of the surfactant-added layer after immersion andwashing of the layer with the solvent (e.g., methyl ethyl ketone, methylisobutyl ketone, toluene, cyclohexanone) of the coating solution for theupper layer is preferably rather higher. The surface energy here ispreferably from 35 to 70 mJ/m².

Preferred embodiments and specific examples of the fluorine-containingsurfactant are described in JP-A-2007-102206, paragraphs [0023] to[0080], and the same applies to the present invention.

Preferred examples of the silicone-based compound include those having asubstituent at the terminal and/or in the side chain of a compound chaincontaining a plurality of dimethylsilyloxy units as the repeating unit.The compound chain containing dimethylsilyloxy as the repeating unit maycontain a structure unit other than dimethylsilyloxy. The substituentsmay be the same or different, and a plurality of substituents arepreferably present. Preferred examples of the substituent include groupscontaining a polyether group, an alkyl group, an aryl group, an aryloxygroup, an acryloyl group, a methacryloyl group, a vinyl group, an arylgroup, a cinnamoyl group, an epoxy group, an oxetanyl group, a hydroxylgroup, a fluoroalkyl group, a polyoxyalkylene group, a carboxyl group oran amino group.

The molecular weight is not particularly limited but is preferably100,000 or less, more preferably 50,000 or less, still more preferablyfrom 1,000 to 30,000, and most preferably from 1,000 to 20,000.

The silicon atom content of the silicone-based compound is notparticularly limited but is preferably 18.0 mass % or more, morepreferably from 25.0 to 37.8 mass %, and most preferably from 30.0 to37.0 mass %.

Preferred examples of the silicon-based compound include, but are notlimited to, “X-22-174DX”, “X-22-2426”, “X-22-164B”, “X22-164C”,“X-22-170DX”, “X-22-176D” and “X-22-1821” (all trade names) produced byShin-Etsu Chemical Co., Ltd.; “FM-0725”, “FM-7725”, “FM-4421”,“FM-5521”, “FM-6621” and “FM-1121” (all trade names) produced by ChissoCorp.; “DMS-U22”, “RMS-033”, “RMS-083”, “UMS-182”, “DMS-H21”, “DMS-H31”,“HMS-301”, “FMS121”, “FMS123”, “FMS131”, “FMS141” and “FMS221” (alltrade names) produced by Gelest; “SH200”, “DC11PA”, “SH28PA”, “ST80PA”,“ST86PA”, “ST97PA”, “SH550”, “SH710”, “L7604”, “FZ-2105”, “FZ2123”,“FZ2162”, “FZ-2191”, “FZ2203”, “FZ-2207”, “FZ-3704”, “FZ-3736”,“FZ-3501”, “FZ-3789”, “L-77”, “L-720”, “L-7001”, “L-7002”, “L-7604”,“Y-7006”, “SS-2801”, “SS-2802”, “SS-2803”, “SS-2804” and “SS-2805” (alltrade names) produced by Dow Corning Toray Co., Ltd.; and “TSF400”,“TSF401”, “TSF410”, “TSF433”, “TSF4450” and “TSF4460” (all trade names)produced by Momentive Performance Materials Inc.

-Translucent Particle-

In the antistatic layer for use in the present invention, varioustranslucent particles can be used so as to impart antiglare property(surface scattering property) or internal scattering property.

The translucent particle may be either an organic particle or aninorganic particle. A smaller variation in the particle diameter leadsto a smaller variation in the scattering property and makes it easier todesign the haze value. The translucent particle is preferably a plasticbead, and a plastic bead having high transparency and giving theabove-described value as a refractive index difference with the binderis more preferred.

Examples of the organic particle used include a polymethyl methacrylateparticle (refractive index: 1.49), a crosslinked poly(acryl-styrene)copolymer particle (refractive index: 1.54), a melamine resin particle(refractive index: 1.57), a polycarbonate particle (refractive index:1.57), a polystyrene particle (refractive index: 1.60), a crosslinkedpolystyrene particle (refractive index: 1.61), a polyvinyl chlorideparticle (refractive index: 1.60) and a benzoguanamine-melamineformaldehyde particle (refractive index: 1.68).

Examples of the inorganic particle include a silica particle (refractiveindex:

1.44), an alumina particle (refractive index: 1.63), a zirconiaparticle, a titania particle and an inorganic particle having hollows orpores.

Among these, a crosslinked polystyrene particle, a crosslinkedpoly((meth)-acrylate) particle and a crosslinked poly(acryl-styrene)particle are preferably used. The refractive index of the binder isadjusted according to the refractive index of the translucent particleselected from these particles, whereby the internal haze, surface hazeand centerline average roughness of the present invention can beachieved.

Furthermore, a binder (refractive index after curing: from 1.50 to 1.53)mainly composed of a trifunctional or higher functional (meth)acrylatemonomer and a translucent particle made from a crosslinkedpoly(meth)acrylate polymer having an acryl content of 50 to 100 wt % arepreferably used in combination, and a combination of the binder and atranslucent particle (refractive index: from 1.48 to 1.54) made from acrosslinked poly(styrene-acryl) copolymer is more preferred.

The refractive index of the binder component (in which a component otherthan a translucent particle is mixed) and the translucent particle ispreferably from 1.45 to 1.70, more preferably from 1.48 to 1.65.

Also, in the present invention, the refractive index difference betweenthe binder and the translucent particle (refractive index of translucentparticle−refractive index of binder) is, in terms of the absolute value,preferably from 0.001 to 0.030, more preferably from 0.001 to 0.020,still more preferably from 0.001 to 0.015. If this difference exceeds0.030, there arises a problem such as film character blurring, reductionin dark-room contrast, or surface clouding. The refractive indexdifference in the range above can be obtained by appropriately selectingthe kind and amount ratio of the binder and the translucent particle.How to select can be easily known in advance by an experiment.

Here, the refractive index of the binder can be quantitatively evaluatedby directly measuring the refractive index with an Abbe refractometer orby measuring a spectral reflection spectrum or a spectral ellipsometry.The refractive index of the translucent particle is determined asfollows. The translucent particle is dispersed in an equal amount insolvents prepared by changing the mixing ratio of two kinds of solventsdiffering in the refractive index and thereby varying the refractiveindex, the turbidity is measured, and the refractive index of thesolvent when the turbidity becomes minimum is measured by an Abberefractometer.

In the case of such a translucent particle, the translucent particle isliable to precipitate in the binder and therefore, an inorganic fillersuch as silica may be added so as to prevent the precipitation. Additionof the inorganic filler in a larger amount is more effective inpreventing the precipitation of the translucent particle but gives anadverse effect on the transparency of the coating film. Accordingly, anorganic filler having a particle diameter of 0.5 μm or less ispreferably added to the binder in an amount of approximately less than0.1 mass % to such an extent as not impairing the transparency of thecoating film.

The average particle diameter (on the volume basis) of the translucentparticle is preferably from 0.5 to 20 μm, more preferably from 2.0 to15.0 μm. If the average particle diameter is less than 0.5 μm, thedistribution of light scattering angle extends to a wide angle andblurring of characters on the display may disadvantageously occur,whereas if it exceeds 20 μm, the thickness of the layer to which thetranslucent particle is added must be increased to cause a problem suchas curl or rise in cost.

Two or more kinds of translucent particles differing in the particlediameter may be used in combination. The translucent particle having alarger particle diameter can impart an antiglare property, and thetranslucent particle having a smaller particle diameter can reduce theroughened texture on the surface.

The translucent particle is blended to account for 3 to 30 mass %,preferably from 5 to 20 mass %, based on the entire solid content of thelayer to which the translucent particle is added. If the translucentparticle content is less than 3 mass %, the effect by the addition isinsufficient, whereas if it exceeds 30 mass %, there arises a problemsuch as blurring of the image or clouding or glaring of the surface.

The density of the translucent particle is preferably from 10 to 1,000mg/m², more preferably from 100 to 700 mg/m².

The antistatic layer for use in the present invention may furthercontain the later-described solvent or other additives. Examples of theadditive which can be further added include: a UV absorber, aphosphorous acid ester, a hydroxamic acid, a hydroxyamine, an imidazole,a hydroquinone and a phthalic acid, for the purpose of suppressing thedecomposition of polymer; an inorganic fine particle, a polymer fineparticle and a silane coupling agent, for the purpose of increasing thefilm strength; and a fluorine-based compound (particularly afluorine-containing surfactant) for the purpose of reducing therefractive index and increasing the transparency.

[Composition for Antistatic Layer]

The composition for the antistatic layer in the present inventioncontains (A) an electrically conductive polymer, (B) a polyfunctionalmonomer having two or more polymerizable groups, (C) at least one kindof a compound (each compound alone or a combination of the compounds)selected from the compound (1), the compound (2) and the compound (3),(D) a photopolymerization initiator, and, if desired, other additives.

The preferred content of each component in the coating composition forforming the antistatic layer is described below. Incidentally, the“content” as used herein indicates a ratio (mass %) of the solid contentof each component to the entire solid content in the coatingcomposition.

The content of the component (A) is preferably from 0.1 to 20 mass %,more preferably from 0.1 to 12 mass %, and most preferably from 0.2 to 5mass %.

The content of the component (B) is preferably from 60 to 99 mass %,more preferably from 75 to 99 mass %, and most preferably from 85 to 97mass %.

The content of the component (C) is, as a total of the compounds 1 to 3,preferably from 0.1 to 10 mass %, more preferably from 0.1 to 5 mass %,and most preferably from 0.1 to 2 mass %.

The content of the component (D) is preferably from 1 to 10 mass %, morepreferably from 1 to 5 mass %.

If the content of the component (A) is less than 0.1 mass %, theelectrical conductivity is low and a sufficiently high antistatic effectcannot be obtained, whereas if it exceeds 20 mass %, the strength of thecoat becomes weak or the coating film is colored, leading to reductionin the transmittance.

If the content of the component (B) is less than 50 mass %, the strengthof the coating film may become weak.

If the content of the component (C) is less than 0.1 mass %, the effectof improving the heat resistance, wet heat resistance and lightresistance cannot be obtained, whereas if it exceeds 10 mass %, thestrength of the coating film may be decreased or deterioration of thesurface state may result, such as whitening of the coating film due tobleeding or generation of surface unevenness on the coating film.

In the case where the coating composition contains a solvent, thesolvent is preferably used such that the solid content concentration inthe coating composition becomes from 1 to 70 mass %, more preferablyfrom 3 to 60 mass %, and most preferably from 40 to 60 mass %.

[Antistatic Layer]

The refractive index of the antistatic layer in the present invention ispreferably from 1.48 to 1.65, more preferably from 1.48 to 1.60, andmost preferably from 1.48 to 1.55. A refractive index in this range ispreferred, because interference unevenness with the substrate can besuppressed and when a low refractive index layer is stacked, the tint ofreflected color can be made neutral.

The film thickness of the antistatic layer is preferably from 0.05 to 20μm, more preferably from 2 to 15 μm, and most preferably from 5 to 10μm. Within this range, both physical strength and electricalconductivity can be satisfied.

The transmittance of the antistatic layer is preferably 80% or more,more preferably 85% or more, and most preferably 90% or more.

The haze of the antistatic layer is, in the case of not containing aresin particle for imparting the antiglare property, preferably 3% orless, more preferably 2% or less, and most preferably 1% or less. In thecase of containing a resin particle to impart the antiglare property,the haze is preferably from 0.1 to 30%, more preferably from 0.1 to 20%.

[Optical Film]

The hardness of the optical film of the present invention is preferablyH or more, more preferably 2H or more, and most preferably 3H or more,in a pencil hardness test with a load of 500 g.

The common logarithmic value (LogSR) of the surface resistivity SR(Ω/sq) of the optical film of the present invention is preferably 13 orless, more preferably from 5 to 12, still more preferably from 6 to 12,yet still more preferably from 6 to 11. By setting the surfaceresistivity to the range above, an excellent dust-proof performance canbe imparted.

In order to obtain such a surface resistivity, the content of theelectrically conductive polymer (A) in the antistatic layer ispreferably from 0.01 to 1.0 g/m², more preferably from 0.05 to 0.5 g/m²,still more preferably from 0.1 to 0.3 g/m².

[Production Method of Optical Film]

The optical film of the present invention can be formed by the followingmethod, but the present invention is not limited to this method. Acomposition for antistatic layer is prepared, and the composition iscoated on a transparent support by a dip coating method, an air knifecoating method, a curtain coating method, a roller coating method, awire bar coating method, a gravure coating method, a die coating methodor the like, and then heated/dried. A microgravure coating method, awire bar coating method and a die coating method (see, U.S. Pat. No.2,681,294 and JP-A-2006-122889) are preferred, and a die coating methodis more preferred.

After the coating, the layer formed of the coating composition is curedby irradiating light, whereby an antistatic layer is formed. If desired,while other layers (for example, the later-described layers constitutingthe film, such as hardcoat layer and antiglare layer) are previouslycoated on the transparent support, the antistatic layer may be formedthereon. In this way, the optical film of the present invention isobtained.

[Layer Configuration of Optical Film]

The optical film of the present invention can be produced by providingan antistatic layer and a single or a plurality of functional layersrequired according to the purpose on a transparent support. The opticalfilm includes an optical film having a hardcoat layer for increasing thephysical strength of the film, and an optical film where layers arestacked by taking into consideration the refractive index, the filmthickness, , the number of layers, the order of layers and the like soas to reduce the reflectance by optical interference.

Incidentally, other functions can be added to the antistatic layer ofthe present invention. For example, an antistatic layer serving also asa low refractive index layer may be formed by adding a compound thatworks out to a low refractive index component. In order to impart a lowrefractive index performance to the antistatic layer of the presentinvention, the configuration described later in “Low Refractive IndexLayer” can be applied. In addition, a hardcoat performance or anantiglare property can be imparted to the antistatic layer of thepresent invention.

Specific examples of the layer configuration for the optical film of thepresent invention are set forth below.

-   -   Transparent support/antistatic layer    -   Transparent support/antistatic layer/low refractive index layer    -   Transparent support/hardcoat layer/antistatic layer    -   Transparent support/antistatic layer/hardcoat layer    -   Transparent support/antiglare layer/antistatic layer    -   Transparent support/antistatic layer/antiglare layer    -   Transparent support/antistatic layer/high refractive index        layer/low refractive index layer    -   Transparent support/antistatic layer/medium refractive index        layer/high refractive index layer/low refractive index layer    -   Transparent support/antistatic layer/hardcoat layer/low        refractive index layer    -   Transparent support/hardcoat layer/antistatic layer/low        refractive index layer    -   Transparent support/antiglare layer/antistatic layer/low        refractive index layer    -   Transparent support/antistatic layer/antiglare layer/low        refractive index layer    -   Transparent support/hardcoat layer/antistatic layer/medium        refractive index layer/high refractive index layer/low        refractive index layer    -   Transparent support/antistatic layer/hardcoat layer/medium        refractive index layer/high refractive index layer/low        refractive index layer        (Transparent Support)

The transparent support in the optical film of the present invention ispreferably a transparent substrate film. The transparent substrate filmincludes a transparent resin film, a transparent resin plate, atransparent resin sheet, a transparent glass and the like and is notparticularly limited. Examples of the transparent resin film include acellulose acylate film (e.g., cellulose triacetate film (refractiveindex: 1.48), cellulose diacetate film, cellulose acetate butyrate film,cellulose acetate propionate film), a polyethylene terephthalate film, apolyethersulfone film, a polyacrylic resin film, a polyurethane-basedresin film, a polyester film, a polycarbonate film, a polysulfone film,a polyether film, a polymethylpentene film, a polyether ketone film, a(meth)acrylonitrile film, a polyolefin, and a polymer having analicyclic structure (e.g., norbornene-based resin (ARTON, trade name,produced by JSR Corporation), amorphous polyolefin (ZEONEX, trade name,produced by Nippon Zeon Co., Ltd.)). Among these, triacetyl cellulose,polyethylene terephthalate, and a polymer having an alicyclic structureare preferred, and triacetyl cellulose is more preferred.

A transparent support having a thickness of approximately from 25 to1,000 μm may be usually used, but the thickness is preferably from 25 to250 μm, more preferably from 30 to 90 μm.

The surface of the transparent support is preferably smooth andpreferably has an average roughness Ra value of 1 μm or less. Theaverage roughness value is preferably from 0.0001 to 0.5 μm, morepreferably from 0.001 to 0.1 μm.

The transparent support is described in JP-A-2009-98658, paragraphs[0163] to [0169], and the same applies to the present invention.

(Hardcoat Layer)

In the optical film of the present invention, a hardcoat layer can beprovided so as to impart the physical strength of the film. In thepresent invention, a hardcoat layer may not be provided, but a hardcoatlayer is preferably provided, because the scratch resistance of thesurface subjected a pencil scratch test or the like is increased.

In view of optical design to obtain an antireflection performance, therefractive index of the hardcoat layer in the present invention ispreferably from 1.48 to 1.65, more preferably from 1.48 to 1.60, andmost preferably from 1.48 to 1.55.

From the standpoint of imparting sufficiently high durability and impactresistance to the film, the film thickness of the hardcoat layer is from0.5 to 20 μm, preferably from 1 to 10 μm, more preferably from 1 to 5μm.

Also, the strength of the hardcoat layer is, in a pencil hardness test,preferably H or more, more preferably 2H or more, and most preferably 3Hor more. Furthermore, in the Taber test in accordance with JIS K5400,the abrasion loss of the specimen between before and after the test ispreferably smaller.

As the binder component for forming the hardcoat layer, the monomersdescribed above with respect to the (B) polyfunctional monomer havingtwo or more polymerizable unsaturated group can be suitably used.

For the purpose of imparting internal scattering property, the hardcoatlayer may contain a matte particle, for example, an inorganic compoundparticle or a resin particle, having an average particle diameter of 1.0to 10.0 μm, preferably from 1.5 to 7.0 μm.

For the purpose of controlling the refractive index of the hardcoatlayer, monomers or inorganic particles having various refractiveindexes, or both of them may be added to the binder of the hardcoatlayer. The inorganic particle has an effect of suppressing curingshrinkage due to a crosslinking reaction, in addition to the effect ofcontrolling the refractive index. The binder as referred to in thepresent invention is a binder inclusive of a polymer produced by thepolymerization of, for example, the above-described polyfunctionalmonomer and/or high refractive index monomer after the formation of thehardcoat layer, and inorganic particles dispersed therein. Use of asilica fine particle as the inorganic particle for controlling therefractive index is preferred from the standpoint of suppressing thetint unevenness due to interference between the support and the hardcoatlayer.

(Antiglare Layer)

In the present invention, separately from the antistatic layer, anantiglare layer may be formed for the purpose of imparting to the filman antiglare property thanks to surface scattering, and preferably ahardcoat performance so as to enhance the hardness and scratchresistance of the film.

The antiglare layer is described in JP-A-2009-98658, paragraphs [0178]to [0189], and the same applies to the present invention.

(High Refractive Index Layer and Medium Refractive Index Layer)

As described above, the refractive index of the high refractive indexlayer is preferably from 1.65 to 2.20, more preferably from 1.70 to1.80. The refractive index of the medium refractive index layer isadjusted to a value between the refractive index of the low refractiveindex layer and the refractive index of the high refractive index layer.The refractive index of the medium refractive index layer is preferablyfrom 1.55 to 1.65, more preferably from 1.58 to 1.63.

As for the method to form the high refractive index layer and the mediumrefractive index layer, a transparent thin film of inorganic oxideformed by a chemical vapor deposition (CVD) method or a physical vapordeposition (PVD) method, particularly a vacuum deposition method or asputtering method, which are a kind of physical vapor deposition method,may be used, but a method by all-wet coating is preferred.

The medium refractive index layer and high refractive index layer arenot particularly limited as long as they are a layer having a refractiveindex in the range above, but those known as the constituent componentcan be used, and specific examples thereof are described inJP-A-2008-262187, paragraphs [0074] to [0094].

(Low Refractive Index Layer)

The optical film of the present invention preferably has a lowrefractive index layer on the antistatic layer, directly or throughanother layer. In this case, the optical film of the present inventioncan function as an antireflection film.

The refractive index of the low refractive index layer is preferablyfrom 1.30 to 1.51, more preferably from 1.30 to 1.46, still morepreferably 1.32 to 1.38. Within this range, the reflectance can be keptlow and the film strength can be maintained. As for the method to formthe low refractive index layer, similarly to the above, a transparentthin film of inorganic oxide formed by a chemical vapor deposition (CVD)method or a physical vapor deposition (PVD) method, particularly avacuum deposition method or a sputtering method, which are a kind ofphysical vapor deposition method, may be used, but a method by all-wetcoating using a composition .for low refractive index layer ispreferred.

The low refractive index layer is not particularly limited as long as itis a layer having a refractive index in the range above, but those knownas the constituent component can be used. Specifically, the compositioncontaining a fluorine-containing curable resin and an inorganic fineparticle described in JP-A-2007-298974, and the hollow silica fineparticle-containing low refractive index coating described inJP-A-2002-317152, JP-A-2003-202406 and JP-A-2003-292831 can be suitablyused.

Among those examples of the layer configuration, the optical film of thepresent invention preferably has a configuration where two layers ofhardcoat layer (antiglare layer)/antistatic layer are stacked on atransparent support. At this time, a low refractive index layer and thelike may be provided on the antistatic layer. Furthermore, two layersabove are preferably formed using a method of simultaneously coating andforming two coated layers in one coating step.

When the film thickness of the antistatic layer is increased so as toobtain a high hardcoat performance while keeping constant theelectrically conductive polymer content in the layer, the total amountof the electrically conductive polymer in the layer is increased andthis tends to intensify the coloration and reduce the transmittance.Also, when the film thickness is increased, the electrically conductivepolymer present in the lower part of the layer does not contribute tothe effect of decreasing the surface resistance and therefore, theamount of the electrically conductive polymer used becomes large. Thanksto the above-described two-layer configuration of a hardcoat layer(antiglare layer) and an antistatic layer containing an electricallyconductive polymer in a high density, an optical film satisfying,all ofhigh hardcoat performance, electrical conductivity and transmittance canbe obtained.

At this time, by simultaneously coating and forming two layers of thehardcoat layer and the antistatic layer in one coating step, highproductivity with a low cost can be achieved. As the method forsimultaneously forming two layer in one coating step, a known method canbe used. Specifically, the method described, for example, inJP-A-2007-293302, paragraphs [0032] to [0056], can be utilized.

[Protective Film for Polarizing Plate]

In the case of using the optical film as a surface protective film of apolarizing film (polarizing plate protective film), the adhesion to thepolarizing film mainly composed of a polyvinyl alcohol can be improvedby hydrophilizing the surface of the transparent support opposite theside having the thin-film layer, that is, the surface on the side to belaminated with the polarizing film.

It is also preferred that out of two protective films of the polarizer,the film other than the optical film is an optically compensatory filmhaving an optically compensatory layer containing an opticallyanisotropic layer. The optically compensatory film (retardation film)can improve the viewing angle characteristics on the liquid crystaldisplay screen.

A known optically compensatory film may be used but from the standpointof enlarging the viewing angle, the optically compensatory filmdescribed in JP-A-2001-100042 is preferred.

In the case of using the optical film as a surface protective film of apolarizing film (polarizing plate protective film), it is particularlypreferred to use a triacetyl cellulose film as the transparent support.

The method for producing the polarizing plate protective film in thepresent invention includes three methods, that is, (1) a method ofcoating layers constituting the antireflection layer on one surface of atransparent support which is previously subjected to a saponificationtreatment, (2) a method of coating the antireflection layer on onesurface of a transparent support and applying a saponification treatmentto the surface to be laminated with a polarizing film or both surfaces,and (3) a method of coating a part of the antireflection layer on onesurface of a transparent support, applying a saponification treatment tothe surface to be laminated with a polarizing film or both surfaces, andthen coating the remaining layer. In the method of (1), the surface tobe coated with the antireflection layer is also hydrophilized, and thismakes it difficult to ensure the adherence between the transparentsupport and the antireflection layer. Therefore, the method of (2) isparticularly preferred.

[Polarizing Plate]

The polarizing plate of the present invention is described below. Thepolarizing plate of the present invention is a polarizing plate having apolarizing film and two protective films for protecting both surfaces ofthe polarizing film, wherein at lease one protective film is theantireflection film of the present invention.

A configuration where the transparent support of the optical film isadhered to a polarizing film, if desired, through an adhesive layer madefrom a polyvinyl alcohol and a protective film is also provided onanother side of the polarizing film, is preferred. On the surface ofanother protective film opposite the polarizing film, apressure-sensitive adhesive layer may be provided.

By virtue of using the optical film of the present invention as apolarizing plate protective film, a polarizing plate excellent in thephysical strength, antistatic property and durability can be produced.

The polarizing plate of the present invention can also have an opticallycompensating function. In this case, it is preferred that out of twosurface protective films, the surface protective film only on onesurface side of either the front surface or the back surface is formedusing the optical film and the surface protective film on the surface ofthe polarizing plate opposite the side having the optical film is anoptically compensatory film.

By producing a polarizing plate where the optical film of the presentinvention is used for one polarizing plate protective film and anoptically compensatory film having optical anisotropy is used foranother protective film of the polarizing film, the bright-room contrastand the up/down right/left viewing angle of a liquid crystal displaydevice can be improved.

Furthermore, the image display device of the present invention ischaracterized by having the antireflection film or polarizing plate ofthe present invention on the outermost surface of the display.

EXAMPLES

The present invention is described in greater detail below by referringto

Examples, but the scope of the present invention should not be construedas being limited thereto. Unless otherwise indicated, the “parts” and“%” are on the mass basis.

Example 1 Preparation Example 1-1

Preparation of Aqueous Solution (A) of Electrically Conductive Polymer

8.0 Gram of 3,4-ethylenedioxythiophene was added to 1,000 ml of a 2 mass% aqueous solution of polystyrenesulfonic acid (molecular weight: about100,000), and these were mixed at 20° C. The resulting mixed solutionwas added to 100 ml of an oxidation catalyst solution (containing 15mass % of ammonium persulfate and 4.0 mass % or ferric sulfate), andreaction was allowed to proceed with stirring at 20° C. for 3 hours.

Subsequently, 1,000 ml of ion-exchanged water was added to the obtainedreaction solution, and about 1,000 ml of the solution was removed by anultrafiltration method. This operation was repeating three times.

Thereafter, 100 ml of an aqueous sulfuric acid solution (10 mass %) and1,000 ml of ion-exchanged water were added to the obtained solution, andabout 1,000 ml of the solution was removed by an ultrafiltration method.Furthermore, 1,000 ml of ion-exchanged water was added to the obtainedsolution, and about 1,000 ml of the solution was removed by anultrafiltration method. This operation was repeated 5 times, whereby anaqueous solution containing about 1.1 mass % of PEDOT·PSS(poly(3,4-ethylenedioxythiophene)·polystyrenesulfonic acid) wasobtained. The solid content concentration was adjusted withion-exchanged water to form a 1.0 mass % aqueous solution. In this way,Solution (A) of electrically conductive polymer was prepared. Solution(A) is an aqueous solution, and the relative permittivity of water is80.

Preparation Example 1-2

Preparation of Acetone Solution (B) of Electrically Conductive Polymer:

After adding 200 ml of acetone to 200 ml of Aqueous Solution (A) ofPEDOT·PSS prepared in Preparation Example 1, 210 ml of acetone wasremoved by ultrafiltration. This operation was repeated once, and thesolid content concentration was adjusted with acetone to prepare a 1.0mass % water/acetone solution. To 200 ml of this solution, 500 ml ofacetone having dissolved therein 2.0 g of trioctylamine was added, andthe mixture was stirred with a stirrer for 3 hours. Thereafter, 510 mlof water and acetone were removed by ultrafiltration, and the solidcontent concentration was adjusted with acetone to form a 1.0 mass %acetone solution. In this way, Solution (B) of electrically conductivepolymer was prepared. The water content of this solution was 2 mass %,and the relative permittivity of the solvent was 22.7.

Preparation Example 1-3

Preparation of Methyl Ethyl Ketone Solution (C) of ElectricallyConductive Polymer:

Methyl ethyl ketone (300 ml) was added to 200 ml of Solution (B) ofPEDOT·PSS prepared in Preparation Example 1-2, and these were mixed. Themixed solution was concentrated at room temperature under reducedpressure until the total amount became 200 ml, and the solid content wasadjusted with methyl ethyl ketone to form a 1.0 mass % methyl ethylketone solution. In this way, Solution (C) of electrically conductivepolymer (Liquid Dispersion (C)) was prepared. The water content of thissolution was 0.05 mass %, and the acetone residual ratio was 1 mass % orless. The relative permittivity of the solvent was 15.5, and the contentof the electrically conductive polymer was 50 mass % based on the solidcontents contained in the solution.

Preparation Example 2

Preparation of Liquid Dispersion (D) of Electrically Conductive Polymer:

Toluene (200 g), 2 g of aniline, 4.2 g of dodecylbenzenesulfonic acid,1.0 g of polyacrylic acid derivative and 0.03 g of 4-methylaniline weredissolved, and 60 g of distilled water having dissolved therein 3.58 mLof 6 N hydrochloric acid was added thereto.

Furthermore, 180 mg of tetrabutylammonium bromide was added to the mixedsolution above, and the mixture was cooled to 5° C. or less.Subsequently, 30 g of distilled water having dissolved therein 5.4 g ofammonium persulfate was added and after performing oxidationpolymerization at 5° C. or less for 4 hours, toluene was removed byvacuum distillation.

Thereafter, the polyaniline precipitate was filtered and washed withwater to obtain the objective polyaniline. The obtained polyaniline wasdispersed in 200 g of toluene and after removing the aqueous layer, theconcentration was adjusted to 2 mass % to obtain Toluene LiquidDispersion (D). (The obtained electrically conductive polymer is acompound where dodecylbenzenesulfonic acid is doped into polyaniline.The relative permittivity of toluene as the solvent is 2.2) The contentof the electrically conductive polymer was about 100 mass % based onsolid contents contained in the solution.

(Preparation of Coating Solution for Antistatic Layer)

Respective components were mixed as shown in Table 1 below, and themixture was dissolved in a mixed solvent of methyl ethyl ketone (MEK)and isopropyl alcohol (IPA) to prepare Coating Solutions HC1 to HC14 forantistatic layer having a solid content concentration of 30 mass %.

TABLE 1 Content (solid content) Liquid Dispersion of ElectricallyPolyfunctional Coating Conductive Polymer Monomer Initiator AdditiveSolution Amount Amount Amount Amount Diluting No. Kind (mass %) Kind(mass %) Kind (mass %) Kind (mass %) Solvent Remarks HC1 Liquid 6 DPHA91 Irg. 127 3 — — MEK(30)/IPA(70) Comparative Dispersion C Example HC2Liquid 25 DPHA 72 Irg. 127 3 — — MEK(30)/IPA(70) Comparative DispersionC Example HC3 Liquid 6 DPHA 90.5 Irg. 127 3 hydro- 0.5 MEK(30)/IPA(70)Comparative Dispersion C quinone Example HC4 Liquid 6 DPHA 90.5 Irg. 1273 Compound 0.5 MEK(30)/IPA(70) Invention Dispersion C (PH-1) HC5 Liquid6 DPHA 90.5 Irg. 127 3 Compound 0.5 MEK(30)/IPA(70) Invention DispersionC (PH-16) HC6 Liquid 6 DPHA 90.5 Irg. 127 3 Compound 0.5 MEK(30)/IPA(70)Invention Dispersion C (PH-19) HC7 Liquid 6 DPHA 90.5 Irg. 127 3Compound 0.5 MEK(30)/IPA(70) Invention Dispersion C (PH-31) HC8 Liquid 6DPHA 90.5 Irg. 127 3 Compound 0.5 MEK(30)/IPA(70) Invention Dispersion C(PH-35) HC9 Liquid 6 DPHA 88.5 Irg. 127 3 Compound 2 MEK(30)/IPA(70)Invention Dispersion C (PA-4) HC10 Liquid 6 DPHA 88.5 Irg. 127 3Compound 2 MEK(30)/IPA(70) Invention Dispersion C (PA-13) HC11 Liquid 6DPHA 88.5 Irg. 127 3 Compound 2 MEK(30)/IPA(70) Invention Dispersion C(HX-5) HC12 Liquid 6 DPHA 88.5 Irg. 127 3 Compound 2 MEK(30)/IPA(70)Invention Dispersion C (HX-11) HC13 Liquid 3 DPHA 93.5 Irg. 127 3 — —MEK(30)/IPA(70) Comparative Dispersion D Example HC14 Liquid 3 DPHA 93.5Irg. 127 3 Compound 0.5 MEK(30)/IPA(70) Invention Dispersion D (PH-19)

Compounds used are as follows.

-   -   DPHA: A mixture of dipentaerythritol pentaacrylate and        dipentaerythritol hexaacrylate (produced by Nippon Kayaku Co.,        Ltd.)    -   Irg. 127: Photopolymerization initiator Irgacure 127 (produced        by Ciba Specialty Chemicals Corp.)        (Preparation of Liquid Dispersion (F) of Hollow Silica Particle)

20 Parts of acryloyloxypropyltrimethoxysilane and 1.5 parts ofdiisopropoxyaluminum ethyl acetate were added to 500 parts of a fineparticle sol of hollow silica particle (isopropyl alcohol silica sol,CS60-IPA, produced by Catalysts & Chemicals Ind. Co., Ltd., averageparticle diameter: 60 nm, thickness of shell: 10 nm, silicaconcentration: 20%, refractive index of silica particle: 1.31), andthese were mixed. Subsequently, 9 parts of ion-exchanged water was addedthereto, and the reaction was allowed to proceed at 60° C. for 8 hours.The reaction solution was cooled to room temperature, and 1.8 parts ofacetyl acetone was added to obtain Liquid Dispersion (E). Thereafter,solvent replacement by reduced-pressure distillation was performed undera pressure of 30 Torr while adding cyclohexanone to keep the silicacontent almost constant, and finally the concentration was adjusted toobtain Liquid Dispersion (F) having a solid content concentration of18.2%. The amount of IPA remaining in the obtained liquid dispersion wasanalyzed by gas chromatography and found to be 0.5% or less.

(Preparation of Coating Solution for Low Refractive Index Layer)

Respective components were mixed as shown in Table 2, and the mixturewas dissolved in MEK to produce a coating solutions for low refractiveindex layer having a solid content of 5%.

TABLE 2 Content (solid content) Coating Binder Polymerization InitiatorHollow Silica Solution Amount Amount Amount RMS-033 Liquid DispersionNo. Kind (mass %) Kind (mass %) Kind (mass %) (amount, mass %) (F)(amount, mass %) Ln1 P-1 28 DPHA 10 Irg. 127 3 4 55 Ln2 DPHA 38 — — Irg.127 3 4 55

Abbreviations in the Table above are as follows.

-   -   “P-1”: Fluorine-Containing Copolymer P-3 (weight average        molecular weight: about 50,000) described in JP-A-2004-45462    -   DPHA: A mixture of dipentaerythritol pentaacrylate and        dipentaerythritol hexaacrylate, produced by Nippon Kayaku Co.,        Ltd.    -   Irg. 127: Irgacure 127, a polymerization initiator (produced by        Ciba Japan)    -   RMS-033: Methacryloxy-modified silicone (produced by Gelest)        (Production of Antistatic Layer)

On a triacetyl cellulose film (TD80UF, produced by Fujifilm Corp.,refractive index: 1.48) having a thickness of 80 μm as a transparentsupport, the coating solution for antistatic layer prepared above wascoated using a gravure coater and dried at 60° C. for about 1 minute.Thereafter, the coated layer was cured by irradiating an ultraviolet rayat an illuminance of 400 mW/cm² and an irradiation dose of 120 mJ/cm²with use of an air-cooled metal halide lamp (manufactured by EyeGraphics Co., Ltd.) of 160 W/cm while purging the system with nitrogento give an atmosphere having an oxygen concentration of 1.0 vol % orless, whereby an antistatic layer having a thickness of 5 μm was formed.In this way, optical films (Sample Nos. 1 to 14) were produced.

(Production of Low Refractive Index Layer)

The coating solution for low refractive index layer was coated using agravure coater on the antistatic layer produced above. The dryingconditions of the low refractive index layer were 60° C. and 60 seconds,and the ultraviolet curing conditions were such that an air-cooled metalhalide lamp (manufactured by Eye Graphics Co., Ltd.) of 240 W/cm wasused at an illuminance of 600 mW/cm² and an irradiation dose of 600mJ/cm² while purging the system with nitrogen to give an atmospherehaving an oxygen concentration of 0.01 vol % or less. In this way,optical films (antireflection films) in which a low refractive indexlayer was formed on the antistatic layer were produced (Sample Nos. 15and 16).

(Evaluation of Optical Film)

Various characteristics of the optical film were evaluated by thefollowing methods. The results are shown in Table 3.

(1) Measurement of Surface Resistance Value

The sample was left standing under the conditions of 25° C. and 60% RHfor 2 hours and then measured using an ultra-insulatingresistance/microammeter, TR8601 (manufactured by Advantest Corp.). Thecommon logarithm (logSR) of the surface resistance value is shown.

(2) Evaluation of Pencil Hardness

As an index of scratch resistance, the pencil hardness evaluationdescribed in JIS K 5400 was performed. The antireflection film wassubjected to moisture conditioning at a temperature of 25° C. and ahumidity of 60% RH for 2 hours and then evaluated using a pencil fortest prescribed in JIS S 6006. In the present invention, the pencilhardness is preferably 4H or more.

(3) Transmittance

The transmittance of light at 550 nm was measured using an UV/visspectrometer (Shimadzu U2400). The measurement is preferably 90% ormore, more preferably 92% or more.

(4) Evaluation of Surface Roughness

Oil-based black ink was applied to the back side of the sample, and thesurface roughness was evaluated by visually observing the sample undersunlight source according to the following criteria.

A: Roughness of the film surface cannot be recognized even whencarefully checked.

B: Roughness of the film surface is recognized when carefully checkedbut is not annoying.

C: The film surface is slightly roughened, and the roughness isannoying.

D: Roughness of the film surface is recognized at a glance and is veryannoying.

(5) Light Resistance Test

Light was irradiated at an output of 180 W/m² for 50 hours by using asuper xenon weather meter, SX-75 (manufactured by Suga Test InstrumentsCo., Ltd.), and then, the surface resistance value was measured by themethod described above.

(6) Heat Resistance Test

In the heat resistance test, the sample was aged in an environment at atemperature of 105° C. and a humidity of 10% RH for 250 hours and then,the surface resistance value was measured by the method described above.

After the light resistance test and heat resistance test in (5) and (6),in view of dust-proof performance, the surface resistance value LogSR ispreferably 13 or less, more preferably from 5 to 12, still morepreferably from 7 to 12, yet still more preferably from 8 to 11.

(7) Integrated Reflectance

The integrated reflectance was measured with a spectral photometer,V-550 (manufactured by JASCO Corp.), after roughening the back surface(surface not having an optical functional layer) of the optical filmwith sand paper to eliminate the reflection on the back surface and thentreating the back surface with black ink, and an average reflectance inthe range of 450 to 650 nm was calculated and used for the evaluation ofantireflection performance.

TABLE 3 Surface Resistance Value (Ω/sq.) Antistatic Low RefractiveBefore After Before Layer Index Layer Integrated Light Light Heat AfterSample Coating Thick- Coating Thick- Transmit- Pencil Reflec- Irradi-Irradi- Treat- Thermal No. Solution ness Solution ness tance (%)Hardness tance (%) ation ation ment Aging 1 HC1 5 μm — — 92.1 3H 4.7 7.914.3 7.9 12.2 Comparative Example 2 HC2 5 μm — — 87.2 B 4.7 4.7 12.1 4.710.5 Comparative Example 3 HC3 5 μm — — not cured — — — — — —Comparative Example 4 HC4 5 μm — — 92.1 3H 4.7 7.3 11.8 7.3 9.7Invention 5 HC5 5 μm — — 92.1 3H 4.7 7 11.2 7 9.2 Invention 6 HC6 5 μm —— 92.1 3H 4.7 6.6 8 6.6 6.7 Invention 7 HC7 5 μm — — 92.1 3H 4.7 6.6 7.86.6 6.6 Invention 8 HC8 5 μm — — 92.1 3H 4.7 6.6 7.8 6.6 6.6 Invention 9HC9 5 μm — — 92.1 3H 4.7 7.3 11.8 7.3 10.3 Invention 10 HC10 5 μm — —92.1 3H 4.7 7.1 11.6 7.1 9.5 Invention 11 HC11 5 μm — — 92.1 3H 4.7 7.211.3 7.2 10 Invention 12 HC12 5 μm — — 92.1 3H 4.7 7.2 10.9 7.2 9.2Invention 13 HC13 5 μm — — 90.2 3H 4.7 8.3 15.1 8.3 13.2 ComparativeExample 14 HC14 5 μm — — 90.2 3H 4.7 7.5 10.9 7.5 8.8 Invention 15 HC6 5μm Ln1 90 nm 94.5 3H 1.5 8.5 9.8 8.5 8.6 Invention 16 HC6 5 μm Ln2 90 nm93.7 3H 1.9 8.5 9.8 8.5 8.6 Invention

As seen from the results above, the optical film having an antistaticlayer containing (A) an electrically conductive polymer, (B) apolyfunctional monomer having two or more polymerizable groups, and (C)at least one kind of a compound selected from the compound (1), thecompound (2) and the compound (3) is assured of strong coat strength,excellent in the transparency and antistatic property and at the sametime, excellent in the heat resistance and light resistance. Also, asfor the optical film where a low refractive index is further stacked onthe antistatic layer, a film having low reflectance and causing littledisturbing reflection can be obtained.

Example 2

(Preparation of Coating Solution for Antistatic Layer)

Respective components were mixed as shown in Table 4 below, and themixture was dissolved in a mixed solvent of methyl ethyl ketone and IPAto prepare Coating Solutions HC15 and HC16 for antistatic layer having asolid content concentration of 30 mass %.

TABLE 4 Content (solid content) Electrically Conductive Poly- PolymerLiquid functional Coating Dispersion Monomer Initiator AdditiveSurfactant Solution Amount Amount Amount Amount Amount Diluting No. Kind(mass %) Kind (mass %) Kind (mass %) Kind (mass %) Kind (mass %) SolventRemarks HC6 Liquid 6 DPHA 90.5 Irg. 127 3 Compound 0.5 — — MEK(30)/Invention Dispersion (PH-19) IPA(70) C HC15 Liquid 6 DPHA 90 Irg. 127 3Compound 1 — — MEK(30)/ Invention Dispersion (PH-19) IPA(70) C HC16Liquid 6 DPHA 90 Irg. 127 3 Compound 1 FP1 0.1 MEK(30)/ InventionDispersion (PH-19) IPA(70) C

In the Table, the abbreviation is as follows.

-   “FP-1”: A fluorine-containing surfactant represented by the    following structural formula.

(Production of Optical Film)

Sample Nos. 17 and 18 were produced in the same manner as Sample No. 1of Example 1 except for changing the coating solution for antistaticlayer to HC15 and HC16.

(Evaluation of Optical Film)

Various characteristics of the optical film were evaluated by the samemethods as above. The results are shown in Table 5.

TABLE 5 Surface Resistance (Ω/sq.) Antistatic Layer Before After BeforeAfter Sample Coating Transmit- Pencil Integrated Surface Light LightHeat Thermal No. Solution Thickness tance (%) Hardness Reflectance (%)Roughness Irradiation Irradiation Treatment Aging 6 HC6 5 μm 92.1 3H 4.7B 6.6 8 6.6 6.7 17 HC15 5 μm 92.1 3H 4.7 C 6.3 7.1 6.3 6.3 18 HC16 5 μm92.1 3H 4.7 A 6.3 7.1 6.3 6.3

As seen from the results above, by further adding a surfactant to theantistatic layer containing (A) an electrically conductive polymer, (B)a polyfunctional monomer having two or more polymerizable groups, and(C) at least one kind of a compound selected from the compound (1), thecompound (2) and the compound (3), high antistatic property can berealized while keeping a very good surface state.

Example 3

An optical film was produced in the, same manner as Sample 6 of Example1 except that a coating solution using Compound (PA-13) in a ratio of 2%or Compound (HX-11) in a ratio of 2% in addition to Compound (PH-19) inCoating Solution HC6 for Antistatic Layer was used. When these sampleswere evaluated, an optical film more excellent in the antistaticproperty, heat resistance and light resistance than those using thecompound (PH-19), (PA-13) or (HX-11) alone was obtained.

Example 4

Sample Nos. 19 and 20 were produced in the same manner as Sample 1 ofExample 1 except for changing the coating solution for antistatic layerto the solution shown in the Table below and applying the coatingsolution to have a film thickness of 12 μm after curing. These sampleswere evaluated in accordance with Example 1.

TABLE 6 Content (solid content) Electrically Conductive PolymerPolyfunctional Monomer Initiator Amount Amount Amount Amount Kind (mass%) Kind (mass %) Kind (mass %) Kind (mass %) Remarks HC17 Liquid 3PET-30 43.5 Viscoat 360 43.5 Irg. 127 3 Comparative Dispersion C ExampleHC18 Liquid 3 PET-30 43.5 Viscoat 360 43.5 Irg. 127 3 InventionDispersion C Content (solid content) Translucent Particle AdditiveAmount Amount Kind (mass %) Kind (mass %) Diluting Solvent Remarks HC178 μm crosslinked acrylic 7 — — MEK(30)/IPA(70) Comparative styreneparticle Example HC18 8 μm crosslinked acrylic 7 Compound (PH-19) 0.5MEK(30)/IPA(70) Invention styrene particle

TABLE 7 Surface Resistance Value (Ω/sq.) Antistatic Layer IntegratedBefore After Before After Sample Coating Transmit- Pencil ReflectanceLight Light Heat Thermal No. Solution Thickness tance (%) Hardness (%)Irradiation Irradiation Treatment Aging 19 HC17 12 μm 91.5 3H 4.6 7.914.8 7.9 12.4 Comparative Example 20 HC18 12 μm 91.5 3H 4.6 6.6 7.8 6.66.7 Invention

As seen above, Sample No. 20 containing a translucent particle in theantistatic layer was assured of strong coat strength, excellent in thetransparency and antistatic property and at the same time, excellent inthe heat resistance and light resistance, and thanks to its antiglareproperty, this was a film causing little disturbing reflection.

The compounds used in the Table are as follows.

PET-30:

A mixture of pentaerythritol triacrylate and pentaerythritoltetraacrylate [produced by Nippon Kayaku Co., Ltd.].

Viscoat 360:

Trimethylolpropane PO-modified triacrylate [produced by Osaka OrganicChemical Industry Ltd.]

8-μm Crosslinked Polystyrene Particle (30%):

An MIBK liquid dispersion obtained by dispersing a crosslinkedpolystyrene particle having an average particle diameter of 8.0 μm[produced by Sekisui Chemical Co., Ltd.] in a polytron dispersingmachine at 10,000 rpm for 20 minutes; refractive index: 1.55.

Example 5

(Preparation of Coating Solution HC-A for Hardcoat Layer

10 Parts by mass of MEK and 40 parts by mass of MIBK were added to 47parts by mass of caprolactone-modified dipentaerythritol hexaacrylate(DPCA-120, produced by Nippon Kayaku Co., Ltd.) and 3 parts by mass ofIrg. 127 (polymerization initiator, produced by Ciba Japan), and themixture was stirred until these were dissolved. The obtained solutionwas filtered through a polypropylene-made filter having a pore size of 5μm to prepare Coating Solution HC-A for hardcoat layer.

(Preparation of Coating Solution HC-19 for Antistatic Layer

Coating Solution HC-19 for Antistatic Layer was prepared in the samemanner as in Example 1 except that the amount of Electrically ConductivePolymer Liquid Dispersion C in Coating Solution HC-6 for AntistaticLayer 19 was reduced to one-third.

(Production of Antistatic Layer)

Sample Nos. 6, 21 and 22 were produced in the same manner as Sample No.1 of Example 1 except that the coating solution for antistatic layer waschanged to the solution shown in the Table below and applied to give afilm thickness of 5 μm, 15 μm, and 15 μm, respectively, after curing.

Also, using Coating Solution HC-A for Hardcoat Layer and CoatingSolution HC-6 for Antistatic Layer, Coating Solution HC-A for HardcoatLayer and Coating Solution HC-6 for Antistatic were coated by acomposite coater having a slot die in one layer and a slide in one layerto have a dry film thickness of 10 μm and 5 μm, respectively, byappropriately adjusting the wet coated amount while conveying the web ata speed of 30 m/min and then dried at 100° C. for 2 minutes. Thereafter,ultraviolet rays were irradiated thereon at an illuminance of 600 mW/cm²and an irradiation dose of 600 mJ/cm² by using an air-cooled metalhalide lamp (manufactured by Eye Graphics Co., Ltd.) of 240 W/cm whilepurging the system with nitrogen to give an atmosphere having an oxygenconcentration of 0.01 vol % or less, whereby the coated layers werecured. In this way, Sample No. 23 was produced. The evaluations wereperformed in accordance with Example 1.

TABLE 8 Antistatic Layer Amount of Hardcoat Layer ElectricallyConductive Electrically Conductive Coating Film Coating PolymerDispersion Film Polymer Dispersion Transmittance Solution ThicknessSolution Content (%) Thickness Coated (g/m²) (%) 6 — — HC6 6  5 μm 0.392.1 21 — — HC6 6 15 μm 0.9 88.6 22 — — HC19 2 15 μm 0.3 92.1 23 HC-A 10μm HC6 6  5 μm 0.3 92.1 Surface Resistance Value (Ω/sq.) IntegratedAfter Pencil Reflectance Before Light After Light Before Heat ThermalHardness (%) Irradiation Irradiation Treatment Aging 6 3H 4.7 6.6 8 6.66.7 Invention 21 5H 4.7 5.4 7.1 5.4 5.4 Invention 22 5H 4.7 8.1 9.6 8.18.5 Invention 23 5H 4.7 6.6 8 6.6 6.7 Invention

As seen from the results above, thanks to the two-layer configuration ofa hardcoat layer/an antistatic layer, a coating film assured of strongcoat strength, excellent in the transparency and antistatic property andat the same time, excellent in the heat resistance and light resistancecan be obtained. Since such a coating film can efficiently exhibitelectrical conductivity with a small amount of electrically conductivepolymer, so that the amount of the electrically conductive polymer usedcan be reduced.

Furthermore, by utilizing a method of simultaneously coating and formingtwo layers in one coating step, the number of coating steps can bedecreased, and low cost and high productivity can be realized.

Example 6

[Evaluation in Liquid Crystal Display Device]

(Production of Polarizing Plate)

A triacetyl cellulose film having a thickness of 80 μm (TAC-TD80U,produced by Fujifilm Corp.) which had been dipped in an aqueous 1.5mol/L NaOH solution at 55° C. for 2 minutes, then neutralized andwashed, and the optical film (saponified) of Examples and ComparativeExamples were adhered to and caused to protect both surfaces of apolarizer produced by adsorbing iodine to a polyvinyl alcohol andstretching it.

(Fabrication of Liquid Crystal Display Device)

The polarizing plate and the retardation film provided in a VA-typeliquid crystal display device (LC-37GS10, manufactured by Sharp Corp.)were removed, and the polarizing plate produced above was insteadlaminated by arranging its transmission axis to agrees with that of thepolarizing plate originally laminated to the commercial product, wherebyliquid crystal display devices having the optical film of Examples andComparative Example were fabricated. Incidentally, the optical film waslaminated to lie on the viewing side.

In the thus-produced polarizing plate and image display device each withthe optical film of Examples, similarly to respective optical filmslaminated, a good surface state free of streak or unevenness andexcellent scratch resistance, antifouling property, dust-proofperformance and adherence were exhibited as compared with ComparativeExamples. Also, in the polarizing plate and image display device eachwith an optical film where a low refractive index is stacked or with anoptical film where antiglare property is imparted, significantly reduceddisturbing reflection of background and very high display quality wereachieved.

What is claimed is:
 1. An optical film comprising: a transparent supportand at least one antistatic layer formed from a composition comprisingat least the following (A) to (D): (A) an electrically conductivepolymer, (B) a polyfunctional monomer having two or more polymerizablegroups, (C) at least one compound selected from a compound representedby the following formula (1), a compound represented by the followingformula (2) and a trivalent phosphorus compound, and (D) aphotopolymerization initiator:

wherein, in the formula (1), Y represents an m-valent group selectedfrom a hydrogen atom, a carbon atom, a heteroatom, a hydroxy group, amercapto group, a substituted or unsubstituted group derived from anamino group, a substituted or unsubstituted group derived from an alkylgroup, a substituted or unsubstituted group derived from an acyl group,a substituted or unsubstituted group derived from an aryl group, asubstituted or unsubstituted group derived from an alkoxy group, asubstituted or unsubstituted group derived from an aryloxy group and asubstituted or unsubstituted group derived from a heteroaryl group, Lrepresents a single bond, a substituted or unsubstituted divalenthydrocarbon group, a substituted or unsubstituted divalent heteroatom ora substituted or unsubstituted imino group, and m represents an integerof 1 or more;

wherein, in the formula (2), R₁ represents a hydrogen atom, an alkylgroup, an acyl group, an aryl group, an alkoxy group, an aryloxy groupor a heteroaryl group, R₂ represents a hydrogen atom, an alkyl group, anaryl group, a heteroaryl group or a sulfonyl group, and the alkyl group,acyl group, aryl group, alkoxy group, aryloxy group, heteroaryl groupand sulfonyl group each may have a substituent; and wherein the compoundrepresented by the formula (1) is a phosphonic acid compound.
 2. Theoptical film as claimed in claim 1, wherein a common logarithmic valueof a surface resistivity (Ω/sq) of the optical film is from 6 to
 12. 3.The optical film as claimed in claim 1, wherein the electricallyconductive polymer comprises at least one of polythiophene, polyaniline,polypyrrole and derivatives thereof.
 4. The optical film as claimed inclaim 1, wherein the electrically conductive polymer comprises at leastone of polythiophene and derivatives thereof.
 5. The optical film asclaimed in claim 1, wherein the electrically conductive polymercomprises poly(3,4-ethylenedioxy)thiophene.
 6. The optical film asclaimed in claim 1, wherein the composition further comprises apolystyrenesulfonic acid as a dopant of the electrically conductivepolymer.
 7. The optical film as claimed in claim 1, wherein, in theformula (1), m is an integer of 2 or more.
 8. The optical film asclaimed in claim 1, wherein the compound represented by the formula (2)comprises at least one compound selected from a hydroxamic acid compoundand a hydroxyamine compound.
 9. The optical film as claimed in claim 1,wherein the trivalent phosphorus compound is a compound represented bythe following formula (I), (II), (III) or (IV):

wherein each of R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹ and R¹²independently represents a hydrogen atom, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted aryl group or a substitutedor unsubstituted heteroaryl group].
 10. The optical film as claimed inclaim 1, wherein the polymerizable group of the polyfunctional monomerhaving two or more polymerizable groups is selected from a substitutedor unsubstituted acryloyl group, a substituted or unsubstitutedmethacryloyl group and —C(O)OCH═CH₂.
 11. The optical film as claimed inclaim 1, wherein the composition further comprises a fluorine-containingor silicon-containing surfactant.
 12. The optical film as claimed inclaim 1, wherein the composition comprises the compound represented bythe formula (1) and the compound represented by the formula (2).
 13. Theoptical film as claimed in claim 1, wherein the composition comprisesthe compound represented by the formula (1) and the trivalent phosphoruscompound.
 14. The optical film as claimed in claim 1 which is anantireflection film and further comprises a low refractive index layerwhich is provided on the antistatic layer directly or through anotherlayer.
 15. An optical film, comprising: a transparent support and atleast one antistatic layer formed from a composition comprising at leastthe following (A) to (D): (A) an electrically conductive polymer. (B) apolyfunctional monomer having two or more polymerizable groups, (C) atleast one compound selected from a compound represented by the followingformula (1), a compound represented by the following formula (2) and atrivalent phosphorus compound, and (D) a photopolymerization initiator:

wherein, in the formula (1), Y represents an m-valent group selectedfrom a hydrogen atom, a carbon atom, a heteroatom, a hydroxy group, amercapto group, a substituted or unsubstituted group derived from anamino group, a substituted or unsubstituted group derived from an alkylgroup, a substituted or unsubstituted group derived from an acyl group,a substituted or unsubstituted group derived from an aryl group, asubstituted or unsubstituted group derived from an alkoxy group, asubstituted or unsubstituted group derived from an aryloxy group and asubstituted or unsubstituted group derived from a heteroaryl group, Lrepresents a single bond, a substituted or unsubstituted divalenthydrocarbon group, a substituted or unsubstituted divalent heteroatom ora substituted or unsubstituted imino group, and m represents an integerof 1 or more;

wherein, in the formula (2), R₁ represents a hydrogen atom, an alkylgroup, an acyl group, an aryl group, an alkoxy group, an aryloxy groupor a heteroaryl group, R₂ represents a hydrogen atom, an alkyl group, anaryl group, a heteroaryl group or a sulfonyl group, and the alkyl group,acyl group, aryl group, alkoxy group, aryloxy group, heteroaryl groupand sulfonyl group each may have a substituent; and wherein theantistatic layer comprises a translucent particle having an averageparticle diameter of from 0.5 to 20 μm on volume basis.
 16. A polarizingplate comprising an optical film as a protective film, wherein theoptical film comprises: a transparent support and at least oneantistatic layer formed from a composition comprising at least thefollowing (A) to (D): (A) an electrically conductive polymer, (B) apolyfunctional monomer having two or more polymerizable groups, (C) atleast one compound selected from a compound represented by the followingformula (1), a compound represented by the following formula (2) and atrivalent phosphorus compound, and (D) a photopolymerization initiator:

wherein, in the formula (1), Y represents an m-valent group selectedfrom a hydrogen atom, a carbon atom, a heteroatom, a hydroxy group, amercapto group, a substituted or unsubstituted group derived from anamino group, a substituted or unsubstituted group derived from an alkylgroup, a substituted or unsubstituted group derived from an acyl group,a substituted or unsubstituted group derived from an aryl group, asubstituted or unsubstituted group derived from an alkoxy group, asubstituted or unsubstituted group derived from an aryloxy group and asubstituted or unsubstituted group derived from a heteroaryl group, Lrepresents a single bond, a substituted or unsubstituted divalenthydrocarbon group, a substituted or unsubstituted divalent heteroatom ora substituted or unsubstituted imino group, and m represents an integerof 1 or more;

wherein, in the formula (2), R₁ represents a hydrogen atom, an alkylgroup, an acyl group, an aryl group, an alkoxy group, an aryloxy groupor a heteroaryl group, R₂ represents a hydrogen atom, an alkyl group, anaryl group, a heteroaryl group or a sulfonyl group, and the alkyl group,acyl group, aryl group, alkoxy group, aryloxy group, heteroaryl groupand sulfonyl group each may have a substituent; and wherein the compoundrepresented by the formula (1) is a phosphonic acid compound.
 17. Animage display device comprising an optical film at an outermost surfaceof the display, wherein the optical film comprises: a transparentsupport and at least one antistatic layer formed from a compositioncomprising at least the following (A) to (D): (A) an electricallyconductive polymer, (B) a polyfunctional monomer having two or morepolymerizable groups, (C) at least one compound selected from a compoundrepresented by the following formula (1), a compound represented by thefollowing formula (2) and a trivalent phosphorus compound, and (D) aphotopolymerization initiator:

wherein, in the formula (1), Y represents an m-valent group selectedfrom a hydrogen atom, a carbon atom, a heteroatom, a hydroxy group, amercapto group, a substituted or unsubstituted group derived from anamino group, a substituted or unsubstituted group derived from an alkylgroup, a substituted or unsubstituted group derived from an acyl group,a substituted or unsubstituted group derived from an aryl group, asubstituted or unsubstituted group derived from an alkoxy group, asubstituted or unsubstituted group derived from an aryloxy group and asubstituted or unsubstituted group derived from a heteroaryl group, Lrepresents a single bond, a substituted or unsubstituted divalenthydrocarbon group, a substituted or unsubstituted divalent heteroatom ora substituted or unsubstituted imino group, and m represents an integerof 1 or more;

wherein, in the formula (2), R₁ represents a hydrogen atom, an alkylgroup, an acyl group, an aryl group, an alkoxy group, an aryloxy groupor a heteroaryl group, R₂ represents a hydrogen atom, an alkyl group, anaryl group, a heteroaryl group or a sulfonyl group, and the alkyl group,acyl group, aryl group, alkoxy group, aryloxy group, heteroaryl groupand sulfonyl group each may have a substituent; and wherein the compoundrepresented by the formula (1) is a phosphonic acid compound.
 18. Anoptical film comprising: a transparent support and at least oneantistatic layer formed from a composition comprising at least thefollowing (A) to (D): (A) an electrically conductive polymer, (B) apolyfunctional monomer having two or more polymerizable groups, (C) atleast one compound selected from a compound represented by the followingformula (1), a compound represented by the following formula (2) and atrivalent phosphorus compound, and (D) a photopolymerization initiator:

wherein, in the formula (1), Y represents an m-valent group selectedfrom a hydrogen atom, a carbon atom, a heteroatom, a hydroxy group, amercapto group, a substituted or unsubstituted group derived from anamino group, a substituted or unsubstituted group derived from an alkylgroup, a substituted or unsubstituted group derived from an acyl group,a substituted or unsubstituted group derived from an aryl group, asubstituted or unsubstituted group derived from an alkoxy group, asubstituted or unsubstituted group derived from an aryloxy group and asubstituted or unsubstituted group derived from a heteroaryl group, Lrepresents a single bond, a substituted or unsubstituted divalenthydrocarbon group, and a substituted or unsubstituted divalentheteroatom or a substituted or unsubstituted imino group; and

wherein, in the formula (2), R₁ represents a hydrogen atom, an alkylgroup, an acyl group, an aryl group, an alkoxy group, an aryloxy groupor a heteroaryl group, R₂ represents a hydrogen atom, an alkyl group, anaryl group, a heteroaryl group or a sulfonyl group, and the alkyl group,acyl group, aryl group, alkoxy group, aryloxy group, heteroaryl groupand sulfonyl group each may have a substituent; and wherein, in theformula (1), m is
 2. 19. A polarizing plate comprising an optical filmas a protective film, wherein the optical film comprises: a transparentsupport and at least one antistatic layer formed from a compositioncomprising at least the following (A) to (D): (A) an electricallyconductive polymer, (B) a polyfunctional monomer having two or morepolymerizable groups, (C) at least one compound selected from a compoundrepresented by the following formula (1), a compound represented by thefollowing formula (2) and a trivalent phosphorus compound, and (D) aphotopolymerization initiator:

wherein, in the formula (1), Y represents an m-valent group selectedfrom a hydrogen atom, a carbon atom, a heteroatom, a hydroxy group, amercapto group, a substituted or unsubstituted group derived from anamino group, a substituted or unsubstituted group derived from an alkylgroup, a substituted or unsubstituted group derived from an acyl group,a substituted or unsubstituted group derived from an aryl group, asubstituted or unsubstituted group derived from an alkoxy group, asubstituted or unsubstituted group derived from an aryloxy group and asubstituted or unsubstituted group derived from a heteroaryl group, Lrepresents a single bond, a substituted or unsubstituted divalenthydrocarbon group, and a substituted or unsubstituted divalentheteroatom or a substituted or unsubstituted imino group;

wherein, in the formula (2), R₁ represents a hydrogen atom, an alkylgroup, an acyl group, an aryl group, an alkoxy group, an aryloxy groupor a heteroaryl group, R₂ represents a hydrogen atom, an alkyl group, anaryl group, a heteroaryl group or a sulfonyl group, and the alkyl group,acyl group, aryl group, alkoxy group, aryloxy group, heteroaryl groupand sulfonyl group each may have a substituent; and wherein, in theformula (1), m is
 2. 20. An image display device comprising an opticalfilm at an outermost surface of the display, wherein the optical filmcomprises: a transparent support and at least one antistatic layerformed from a composition comprising at least the following (A) to (D):(A) an electrically conductive polymer, (B) a polyfunctional monomerhaving two or more polymerizable groups, (C) at least one compoundselected from a compound represented by the following formula (1), acompound represented by the following formula (2) and a trivalentphosphorus compound, and (D) a photopolymerization initiator:

wherein, in the formula (1), Y represents an m-valent group selectedfrom a hydrogen atom, a carbon atom, a heteroatom, a hydroxy group, amercapto group, a substituted or unsubstituted group derived from anamino group, a substituted or unsubstituted group derived from an alkylgroup, a substituted or unsubstituted group derived from an acyl group,a substituted or unsubstituted group derived from an aryl group, asubstituted or unsubstituted group derived from an alkoxy group, asubstituted or unsubstituted group derived from an aryloxy group and asubstituted or unsubstituted group derived from a heteroaryl group, Lrepresents a single bond, a substituted or unsubstituted divalenthydrocarbon group, and a substituted or unsubstituted divalentheteroatom or a substituted or unsubstituted imino group;

wherein, in the formula (2), R₁ represents a hydrogen atom, an alkylgroup, an acyl group, an aryl group, an alkoxy group, an aryloxy groupor a heteroaryl group, R₂ represents a hydrogen atom, an alkyl group, anaryl group, a heteroaryl group or a sulfonyl group, and the alkyl group,acyl group, aryl group, alkoxy group, aryloxy group, heteroaryl groupand sulfonyl group each may have a substituent; and wherein, in theformula (1), m is 2.